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THE RARE THE RARE

BREED BREED

Hannah Hammond Hannah Hammond

Jacob Cohen Jacob Cohen

RYAN LEAF RYAN LEAF

OUTLIER

EDITORIAL

PUBLISHER&

MANAGINGEDITOR KATHYLOVE

COPYEDITOR MELISSACOHEN

CONTENT&ARTDIRECTOR VICTORIAWALLING

DIRECTOROFPHOTOGRAPHY LISABOUSQUET

ASSISTANTPHOTOGRAPHER CLAIBORNE“BO”LEAF

CONTRIBUTINGWRITERS MEGANGROSS MICHELLEMACECURRAN AMANDAMCCREIGHT ANTONIONEVES JAREDARMSTRONG PETERSCHALLER AMANDASELLERS CHRISSCHEMBRA MANDOLENMULL,PH.D. KOFIDOUHADJI

Photo Credit: Eileen Gu’s Instagram

Olympic gold medalist, freestyle skiing trailblazer, and global ambassador for athletic excellence and cultural pride

THEY CALLED US BLACK SHEEP LIKE IT WAS AN INSULT.

As if standing apart from the herd meant we’d lost our way But if you’ve ever been one, you know the black sheep sees the horizon first.

This issue of Outlier Magazine is a celebration of those who don’t blend in The innovators, the misfits, the ones who make people uncomfortable before they make them think.

Our stories this season trace the bright side of being different, the creative courage it takes to question what’s always been done, and the quiet strength it takes to keep going even when no one else understands your vision.

Because history has always been rewritten by the black sheep They’re the ones who refuse to conform to the mold, disrupt the tradition, and turn their contrarian nature into their legacy. From entrepreneurs building on instinct instead of approval, to artists transforming alienation into beauty, to leaders redefining what success looks like when you stop chasing belonging. This issue is a toast to them. To us. So here’s to the black sheep, the bold, the brave, the beautifully misunderstood You weren’t made to blend in You were made to lead the flock someplace new.

Scott MacGregorPublisherandEditor-in-Chief

HANNAH HAMMOND with...

Founder & CEO of HB Capital, The Best Available Resource for Financing CRE Nationwide, Speaker & Podcast Host

Q:Youhaveshared,Hannah, thatmoneyoncerepresented freedommorethanluxuryfor you.What’stheearliest memorythatreallycrystallized thatbelief,andhowdidit shapethepersonthatyou’d become?

WhenIwassevenyearsold,Imeta friendwhohadallthethingsthatwe didn’thaveinmychildhoodorinmy environmentgrowingup.Shehada happyfamily Shehadabeautiful house.Shehadhorses.Shehad lovingsiblings.Theywenton vacations.

Myhouseholdwasaverydifferent story.Itwasalotofanxiety,alotof tension,alotofscarcity.Wedidn’t havealotofmoney.Mydadworked atapawnshop.Hestilldoestoday. Mymomwasanight-shiftgrocery bagger.Theyhadaverychallenging marriage.MybrothersandIhada verychallengingrelationship.

Sotheeasiestequationformeto decidewhatwasdifferentbetween usandthemwasthattheyhad moneyandwedidnot.Thatwasthe

earliest memory, at seven, when I was like, “Oh, freedom, happiness, love equals become wealthy.”

That’s what started my pursuit of becoming wealthy When I became a millionaire by 25 years old and I didn’t have that happiness and that love and all of the things that I necessarily thought it would bring me, that’s what led me down the path of personal development and realizing, “Okay, there’s more to this life. There’s more to love. There’s more to happiness than just money alone.”

“WHENYOUCANSHOWUPASYOURAUTHENTICSELF,WHENYOU

-HANNAHHAMMOND

Money does play a huge factor We live in a world where money is a means to transact. You need money to be able to have time freedom. Money buys you access to feel good about yourself, do experiences that make you happy, get in circles and rooms and networks with really amazing people that light you up and help you grow.

So it’s very important, but it’s not the only thing. Unfortunately, a lot of people work their whole life pursuing this financial goal, thinking that it’ll fill this void in them, and they don’t ever get there. Or they get there but they don’t feel it, so then they just set a bigger financial goal, thinking, “Oh, well, I just need more of it.”

That’s something I’m very passionate about: understanding the pursuit of fulfillment and the pursuit of financial freedom. The internal freedom and the financial freedom, they’re correlated, but they really are two separate pursuits We can’t abandon one in the pursuit of another, because both of them are really needed to have the full experience of life, reach our highest potential, in my perspective

Q:Ifyouhadtotellyourorigin

conceptwin,whatwould thosesceneslooklike?

Amomentofstrugglewaswhenmy dadwouldn’tbuymeanicecream conewhenIwassixyearsold,andI wantedtohavefinancialfreedomsoI couldbuythethingsthatIwantedin lifeandhavethelifethatIwanted, pairedwithalotofthefeelingsof insecurityandlowself-worthdueto thatwholeenvironment.

Theturningpointwasrealizingthat moneydidn’tbuyallthehappiness thatIwashopingforwhenIwas25 yearsoldandhadbecomea millionaire. Thentheothersideofgrowthand transformationwasreallydivinginto thepersonaldevelopmentand healingthethingsinsideofme.

Healingtheinsecurities.Findinglove withwhoIwasandcompassionwith whoIwas.ForgivingthosethatIwas holdingontoalotofresentmentand angertowardsthatIdidn’teven

know, because I was just covering it up with work And realizing how bright it was on the other side when you can be whole and really get your values.

When I understood what my values were, became aligned with them, and started to only attract things into my life that were aligned with my values, and decline things that were not, I really had a clear picture of my true north and a wholeness within me without that anger or fear or resentment. That’s when everything started to flourish in my life financially, personally, and in every area. them poorer.”

Q:Howintheworlddidyou becomeaself-made millionaireat25?Tellusalittle bitaboutthat,butthenalso tellusthatrealizationthatit’s stillnotenough,andhowyou definetruewealth.

IreadRichDadPoorDadbyRobert KiyosakiwhenIwas13yearsold,and he’snowaverydearfriendand mentorofmineinreallife.Butthat bookwastheturningpointof thinking,“Okay,Ineedtobuyassets, notliabilities.”

Healwayssays,“Therichbuyassets andthepoorbuyliabilities.Therich usegooddebttogetricherandthe pooracquirebaddebt,whichmakes

He also talks about “mind my own business.” It’s important to be entrepreneurial and have control over your business, your outcomes, your wealth, whether it’s a sales position or whether it’s your own company, and multiple layers in between.

Then he said you have to be good at public speaking, sales, and capital raising if you really want to grow and scale.

So I learned those lessons when I was 13 years old, and I really took them to heart. I got my real estate license at 18, sold a commercial building that summer before I started engineering school, and then used that commission to buy my first property and renovate it.

ThenIsoldanotherbuildingand usedthenextcommissiontobuy anotherproperty,andthenIrented thatoneoutonAirbnb.SoIjustheld assets,addedvaluetothem,and startedtobuild.

Ilivedveryfrugallyuntilmycash flow,justlikehetaught,wasenough topayforsomeofmyliabilities.

BythetimeIwas25,Ihadbecomea millionairethroughmyasset appreciation,andIwasmaking prettygoodmoneyselling commercialrealestate.It’sa commission-basedjob Iwasan engineerforaperiodoftimetoo,but Iwasalwaysdoingrealestateonthe side,bothsellingandinvesting.

SotherecipeIfollowedwas compoundingyourinvestments, livingbelowyourmeans,andletting yourassetspayforyourliabilities.

Q:Mostpeoplewouldthink, “Millionaireat25,you’reliving thelife.”Butthatwasn’tthe case?

No.No.

Iwasdeeplydepressed,highanxiety, stilldiagnosedanxiety,depression, takingantidepressants.Iwentto engineeringschool,graduatedearly, workedincorporateAmerica. Amazing,absolutelyincredible company.Butultimately,Iwasjust

searchingforsomethingthatI couldn’tfillinsideofme Just searching.

Andthentheanswerwasalways moreandmoreandmore.

SoIleftalotofthings.Ileftmyjob, boughtaone-waytickettoHawaii, didn’tfindhappinessinHawaii.

That’swhenmymomtoldme, becauseIwaslike,“Mom,I’mstill miserable.I’minparadise.I’m lookingatthebeautifulocean.I’m livingoffmyrentalincome.I’m25 yearsold”

Actually,atthetime,Iwasn’teven25 whenImovedtoHawaii.Atthetime, Iwasalreadyabletotechnically retirefrommyrentalincome Ithink Iwas22whenImovedtoHawaii.I hadafewpropertiesandtheywere doingprettywell.

Anyway,shesaid,“Honey,wherever yougo,yougowithyou.”

AndIwaslike,“Oh,well,I’mthe problem.”Like,Ican’tescape anything.NomatterwhatIdo,I’m stillhere Iwasn’tcomfortablewith myself

Ittookmeawhilelongerofjust chasingdifferentthings:different relationships,differentbusiness ideas,differentwhatever

Ultimately,IrealizedthatI’m

continuouslythecommon denominatorintheoutcomesinmy life Beingavictimorpointingthe fingeratanybodyelseisnotgoingto serveme.IfI’mgoingtopointthe finger,itneedstobeatmyself, becauseIcancontrolmyselfandI can’tcontroltheseotherthings aroundme.ButifIcanbecomea betterversionofmyself,thenmaybe I’llattractbetterthingsintomylife.

At25,Ihiredmyfirstcoach Hewas anenergeticintelligencecoach, whichIwouldhaveneverhired.Iwas veryscarcitymindset:save everything,reinvest,afraidtospend anymoney

Butaverysuccessfulrealestate developerthatIknewreferredmeto thiscoach.He’slike,“Youhaveto workwithhim Trustme”And becauseItrustedhim,Iwaslike, “Okay,cool.WheredoIsignup?”

Sothatwasmyfirstcoach,andhe’s theonethattaughtme Hesaid,“The intentionbehindeverythingthat you’redoingiswrong.Yourintention isbecauseyou’retryingtolove yourself,oryou’retryingtogetlove, andyou’renevergoingtogetgood outcomesifthat’syourintention. Yourintentionneedstocomefrom love.”

becauseyoulovethisgiftthatyou’ve beengiven.

Hesaid,“Youroutcomecanonlybe asgreatastheenergeticstatein whichyouinitiatetheaction.”

SoifIwasdoingeverythingfroma stressed,anxious,fearful,scarcity, neuroticstate,Iwasnevergoingto getgoodoutcomes,nomatterhow manyhoursIputin.Andsure,on paper,IwasbuyingassetsandIwas makingmoney,butIwasn’tgetting goodoutcomesbecauseIwas miserableandIwassuicidal.

That’swheremymainpriorityshifted from,“HowdoIjustmakemore moneyanddomoreworkandstay busiertoavoidthepainIfeelinside?” to,“HowdoImaintainapeak energeticstate90%ofthetime?”

Hesaidthat’sanA.Ifyougeta90% to100%,youknow,ifthere’s10%it

Like,youdothesethingsbecause youloveyourself,becauseyoulove life,becauseyouloveotherpeople,

doesn’treallymatter There’sgoing tobe10%oflifethat’svery challengingandyouneedthattime togrieveandbeinabadstate, becauseit’slife.You’renotgoingto beperfectallthetime

Butifyoucanfeelinthegreenzone, inaflowstate,90%ofthetime,then howcouldyoueverbeonyour deathbedandhaveanyregretsin yourlife?Regardlessofwhatyou accomplishfinanciallyoronpaperor anythingelse,ifyouknowthatyou livedinthegreenzone,youknow youlivedyourbestlife,andthat’sthe ultimategoal.

SoIbecameobsessedwiththat,and Istartedtoshifteverythinginmylife. Firstwasdoinganenergyaudit throughouttheday:whatmakesme feelexpansiveandwhatmakesme feelcontracted,whatmakesmefeel excited,whatmakesmefeelbored, whatmakesmefeeljoy,whatmakes mefeeloverwhelmandfear.

Istartedtoleanintothethingsthat mademefeelexpansiveandleave outthethingsthatmademefeel contracted.

ThatwasthefiancéIwasengaged to.Ilefttherelationship. ItwascertainclientsthatIwas workingwithbecauseofthemoney potential,buttheybroughtmeout ofthestate,soIdroppedthose clients.

Itwascertainteammembersor employeesthatIwasworkingwith Theydidgoodwork,buttheywere miserabletobearound.Iletgoof thosepeople.

AsIstartedtodomoreofwhatmade mefeelexpansiveandallowedmeto stayinthegreenzoneandbecome moreintentionalaboutthat,moreof thatstuffstartedtoflowintomylife. Allofasudden,amazingpeople startedcomingintomylife,and amazingopportunitiesstarted comingintomylife,becausemy actionswereinitiatedinapeakstate, somyoutcomeswereexactlyasI wantedthemtobe,versusprior whenmyactionswerestartingina badstate.

Q:Youmayhavejust answeredthisquestion,but I’mgoingtoaskitanywayand seeifyou’vegotmoreforus. You’vebeenvocalaboutinner

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healingandconsciousness work.What’sonespecific practiceorbreakthroughthat haschangedhowyoushow up? Thatwasit:committingtolivingin thegreenzonenomatterwhatIdo.

Partofthatwasreallyrefiningmy corevalues Iusedtostruggle makingdecisions.Ididn’tknowwhat therightdecisionwas.AmIafraid justbecauseIhaven’tdoneitbefore, oristhismyguttellingme,“Thisis bad Run”?Thereweresomany opportunities.Whichone’stheright one?Thispersonseemsgreat,but aretheygoingtoscrewmeover?I struggledwiththat.

ButasIbecamesoalignedwithmy truenorth,withmyvalues,with what’simportanttomeinevery singleareaofmylife,itchanged everything Ihavea50-pageplaybookofmytrue north,ofexactlyeveryarea: relationally,financially, entrepreneurially,spiritually,allof thedifferentthings AndIhavean outlineofmyvalues,ofwhatIdon’t waveronnomatterwhat.

Sonow,whenIhavenew opportunitiesorwhenIhave decisionstomake,Icantrustmy

intuition so deeply, because I am so aligned and so connected with myself and with what’s important to me and with what my values are

If it’s not a “hell yes,” it’s a hard no. Before, when I wasn’t aligned, I couldn’t trust my intuition, because there was all this fear and anxiety and disconnection within me. My mind or my gut, or whatever, was always lying to me.

Committing to the green zone and staying in that peak state of energy made me understand this: no one in this world can control how I feel but me I refuse to sell my energy for that cheap, to sell how I feel for that cheap.

So I choose how I feel I choose how I show up

RegardlessofwhatstormsI’min, becausetherearealwaysstorms, everyday,that’swhatwedoasCEOs: wegetpresentedstormsallday, issuesthatnobodyelsecansolve.I’m like,“Okay,I’mgoingtobeinthe stormnomatterwhat,butIchoose howIfeelasInavigateit.Nobody elsedoes.”

Thesituationcanbethesame,but howIshowupandhowIfeelinside isdifferent.

Thatabilitytoemotionallyand energeticallyregulatemyselfto handlethekindofpressurethatI faceeverydayhaschangedmylife, becausenowitdoesn’tfeellike pressure.Istillfeelfree.

Nowit’sjust:ImakedecisionsandI takeactionsteps,andIknow everythingI’mdoingisaligned. BecauseI’mnottiedtotheoutcome totrytofillsomethingmissinginside ofme,ifthedealdoesn’tgo,thedeal doesn’tgo.I’mnottiedtothe outcome.Iloveit.It’salignedwith mytruenorthandwhatIwantto build,butIdon’tneedthatoutcome tofeelwhole,becauseI’malready wholeandI’menjoyingthejourney.

AsIsetbiggoalsanddreams,I refusetosacrificemygreenzone commitmentinthatpursuit

SoImightsaythingslike,“Yeah,I wanttobeabillionaire.Iwantto

buildabillion-dollarorganization.I wanttohelpyoungchildrenlearn entrepreneurshipandbuildwealth andfinancialintelligence.Iwantto makesuchabigimpactonthe world.ButIwillnotsacrificemy greenzoneinthatpursuit”

IfIrecognizethatI’mbecoming disconnectedorofftrack,orI’m feeling,likerightnow,“Ohmygosh, I’mworking20hoursaday It’stoo much,”andI’mstartingtofeelthat anxiety,I’mlike,“Okay,slowdown, stepback,breathe.”

Idon’tsacrificemygreenzone becauseIalreadyamwhole.Idon’t needtodoallthis.Icanslowdown.I don’tneedtogoatthiscrazypace.I don’tneedtosayyestoeverysingle thing

Havingtheawarenessandbeing abletosaynoandrecalibrateisthe importantthing.It’sthatconstant dailyrecalibrationtobeableto coursecorrectsoyoudon’tlose yourselfinthepursuitofthething.

Youdon’tsacrificethethingthatyou wantedinthepursuitofthething thatyoualreadyhad.It’slike,“Don’t sacrificewhatyouneedtogetwhat youdon’tneed.”Iforgettheexact quote,butthat’stheidea.

Q:Youbuiltmanybusinesses, butyouarekindofallchipsin rightnowwithtwo businesses:TheFirmandHB Capital.Tellusalittlebit aboutthosetwocompanies thatyou’rebuildingtoday.

HBCapitalismymainone That’smy nationaldebtandequitycapital advisoryfirm.

Ultimately,whatwedoiswesource andsecurethebestfinancingfor commercialrealestateinvestorsand developersacrossthecountry.We doluxuryresidentialtoo,basically anyinvestmentproject,whetherit’s anacquisition,newconstruction,or refinance.

We work with about 10,000 lenders in our database. I’m very techforward, so we have a pretty cool AI lender-matching platform. Then we also have a team that’s been at all the big firms, and they’re very experienced with very deep-rooted relationships too So it’s still relationship-rooted but tech-forward.

AI is super exciting as we can be more efficient and provide a better level of service as those tools continue to progress.

Pretty much anything from a millionand-a-half dollar loan to a $200 million loan. Now we’re seeing bigger ones for data centers and things like that.

So we aim to be the one-stop capital partner for real estate investors across the country. That’s that company.

Then The Firm is my Arizona company, and that’s a commercial and residential real estate brokerage. We’re a boutique firm and just serve Arizona in that one.

It’s exciting, and we’re trying to lean heavily into both debt and equity because a lot of our clients that we place the debt for, they’re looking for a co-GP equity partner, or family office, or PE firm, or institutional capital to come in and partner with them on the deals

Photocredit:HBCapital’sInstagram

Wearecontinuingtobuildoutthat platformsowecantrulybeafull capitalpartnerforthefullcapital stack,akindofone-stopshopon thatend.

Q:YoulaunchedHBCapitalin adownmarket.Whatwasone oftheboldestdecisionsyou madethatpeoplearoundyou probablydidn’tunderstandat thetime?

Launchinginadownmarket,and alsonotcomingfromcapital markets Idon’thaveafinance degree.Ihaveanengineering degree.I’veneverworkedincapital markets.

Iownedarealestatebrokerage, whichiscommercialrealestaterelatedbutnotonthecapital marketsside.

Alsobeingbootstrapped,Idon’thave anyinvestors.It’sjustme,andI’m fundingitmyself,andcompeting withCBREandJLLandColliers, thesemassivepublicconglomerates, asmycompetitors.

Butit’sbeenreallyexciting.It’sbeen reallyfun

Wehaveapproximately$2.5billionin thepipelinealready,injustavery shortperiodoftimethatwe’ve launched Somybiggestconstraint rightnowisjustfindingamazing peoplethatarealignedwiththe valuesandthestandardsof excellence.

There’salotofaveragepeopleout there,andIdon’thireaverage people,becauseIknowthatwe’re onlyasstrongasourweakestteam member Andthatdoesn’teven meanskillset.Thatmeansvalues.

That’swhatI’mfocusedonright now:continuingtobuildthose relationships That’smoredifficult becauseIdidn’tcomefromcapital markets.Ihaven’tbuiltthosedeeprootedrelationshipswithreallygreat debtandequityadvisorsoverthe years

That’sthebiggestthingthatIthink willnotallowmetogrowatthepace thatIwanttogrow,becausethedeal flowisthere Ihavegreat relationshipswithdevelopers.Ibuilt

thoseforalongtime.

Butit’sreallyfun,andI’menjoying thejourney.Successisfoundin inefficiencies.

Sojustsolvingfortheinefficiencies inthecapitalmarkets,andbeing abletodoitveryquickly,because thenicethingis,becausewe’re boutique,becausewe’renimble, becausewe’retech-forward,and becausethefounderisamillennial, engineer,techperson,wecanadapt veryquicklytothenewtoolsout there.

Myfirstprojectbackin2014was buildinganautonomousrobotin engineeringschool.Wecan implementanewtoolinthe companytoday.Wedon’thavetogo throughapprovalandboardand complianceandallthisstuff.

It’slike,“Hey,thisworks.Thishelps people.Thishelpstheteamservethe clientsbetterandbemoreefficient, productive,andliveintheirgreen zonebetter.Wecanimplementthat today.”Andthat’sbeenreallyhelpful.

hadsofar?

That’ssohard There’ssomanygreat ones.Idon’tthinkit’sone conversation.Ithinkit’smoreofa theme. It’snotuncommonthatmyguests willtearupontheshowandgetvery vulnerable,andIlovethatbecausea lotofshows,peoplegetonand they’relike,“Oh,I’mreallycoolandI builtabillion-dollarfundandI manage$3billion,”or“Ihavea$500 millionwhatever.”

That’samazing.It’sawesometo highlightthesuccessandwhat they’veaccomplishedandwhatthey managedandallthatstuff.

ButItrulyfindthatit’sreallyhardto besuccessful It’sreallyhardto createsomethinggreat.It’sreally hardtoleadandgrowandscaleand operateacompany.

Iliketodig.Ithinkit’smoreofan innerbattlethanitisanouterone.I thinkit’smoreabouttheinner strength,theinnerperseverance,the innertransformation.Theemotional andtheenergetic,allofthat,playsa biggerroleinsuccessthanthe skillsetofhowdoyoudoX,Y,Z.

Nowknowledgeischeap.Youcan learntheskillsetprettymuchforfree throughAInow.Butit’s:howdoyou internallybeabletoleadpeople, communicate,buildrelationships, buildtrust,beaccountable,stickto yourcommitments,knowwhat’s signalversuswhat’snoise,andwhat tofocusonwhenyouhavesomuch informationandsomany opportunities?

That’swhatstuckout.Alotof entrepreneursandalotofvery successfulpeople,justliketherestof us,andprobablymoreso,haveavery deep-rootedunworthinessor insecurityorfearthatinitially stemmedtheirmassivepursuitfor success

ManyofthepeopleI’veinterviewed havebeendownthatsamepathas mewheretheyrealize,“Oh,thisisn’t everything Iwanttotransform individually.”

actualizationisattheverytop

It’sbeautifultoseethatallofushave thesestruggles.Allofusarereal people Allofushavethese vulnerabilitiesandthesefearsinside ofus.

Butwhenyoucanhitthelevelof successandrealizethatyouhaveto hitittounderstandthatitwon’t makeyouhappy,unfortunately, becauseuntilyouhitit,youjust believe.You’reholdingontothat.

Thenonceyouhitit,youstarttoseek otherthings:philanthropyand givingback.

AlotofourclientsandpeopleI’ve hadontheshow,they’vedoneplant medicinejourneys,ortheygetinto morefaithandspiritualityandstart tosurrendermore,orleanonGod more,orhavesomeofthesereally beautifulexperiences

Sothat’sreallythetheme:the journeyofself-actualizationand whatthereisintheworldtobe experiencedbeyondjusttheouter successthatsomanypeopleare searchingfor.

ThisisMaslow’shierarchyofneeds, right?Youhavetohittheselevelsto starttoevenunderstandwhatthe nextlevelis.That’swhyself-

Q:Yourpersonalbrandiskind oflikeamashupbetweenMel RobbinsandRobertKiyosaki. Whatdoyouconsciously

borrowfromeachofthose worlds?

Ithinkthestigmaaround consciousnessandpeaceand happinesshasbeenmoreBuddhism, right?It’slike,“Avoiddesire.Avoid thematerialisticWesternworldand allofthatifyouwanttohavepeace, fulfillment,allthesethings”

Andthentheothersideofthe materialisticworldwaslike,“Suffer. Justsufferandgrindandworkand getallthesethingsandmakebillions ofdollars,”right?They’vealways contradictedeachother,likeoiland water.

Somymissionis:whycan’twehave both?

Whycan’twecreategreatAmerican thingsandbusinessesandhave wealthandenjoytheexperiences andtheluxurythingsoflifeand

pursuebiggrandgoals,andalso havepeaceandwisdomand connectionandfulfillmentandcalm andgroundedness?

Whycan’tweblendboth? Ithinkweneedtoblendboth, becauseIdon’tthinkyoucantruly reachyourhighestpotentialor realizethebestlifethatyoucould possiblyliveifyoudon’thaveboth

That’sthemessageandthemission I’monasIsharemyjourneyofthat pursuit,becauseit’sdifficult.It’sa difficultbalance Theyseemto conflicteachother,butreally,they helpeachothersomuch.

Istudyspiritualleaders.Imeditate.I dobreathwork I’vetakenthings fromBuddhistpractices,justthese differentthings.Iliketolearn.

ButI’malsodeeplyrootedinfaith,in JesusChrist,inGod Ihaveagreat relationshipwithGod. Andbusiness.I’malwaysinto businessandskillsandtechnical growth:growthebusiness

Whenweblendallofthattogether andwehavethisbalance,andIdon’t likethewordbalancebecauseit’s reallymorealignment,whenwe havethealignment,thenwecan trulythriveandbuildwhatever.

Ibelievewecancreatewhateverwe want.Whateverwewanttocreate, wecouldcreateit

Peoplejustdon’tbelievethattobe true.Iknowit’struebecauseI’vehad nothing.Icamefromnothing. IwasblessedtobeborninAmerica

Thatisonething.ButIknowlotsof peoplethatwereborninother countriesthatstillmadeit,still createdwhatevertheywantedin theirlifeandmadeithappen.

Thatintersectionbetweenthe connectedness,thealignment,the groundedness,andthepersonal developmentpairedwiththe businessskillsisthebestthing.

Q:Whenyouzoomout10,20 yearsfromnow,whatdoyou wantpeoplewhohavenever metyoutofeelaboutyouand whatyou’vebuilt?

ThatIbelievedinthem Iallowed themtobelieveinthemmorethan theydidwhentheymetme.

Andthattheywentofftotransform theirlivesandtrulycreatebeautiful livesofabundanceandhappiness andallofthethingsthattheycould dreamof.

theywentanddidthat. WATCH THIS NEXT PART!

What are non-negotiables in your life? I know the green zone is one of them.

Tune in to Scott and Hannah’s conversation about this question here:

Thattheybelieved,becauseofme, thattheycouldhaveitall,andthen

Q:We’reintheYearofthe Horse,you’realifelonghorse lover.Wheredidthatcome from?

WhenIwassevenyearsoldandI metmyfriend,sheintroducedmeto thewealthyfamily,therichdad family,right?Shehadhorses.

They’resostrong,butthey’reso gentle They’rebeautifultowatch They’rekind.

Imaybegoingbrunettethisyear.

WhenIwasgrowingup,horseswere whereIfoundmypeace Theywere mysafeplace Humanswerenotmy safeplace.

WhenIwouldlookintoahorse’s eyes,orrideahorse,orwalkwitha horse,orbrushthehorse,Ijustfelt freeandcalmandconnected.

Theyactuallymatchtheirheartbeat toahuman’sheartbeatwithin20 feetfromthem Sothey’revery connectedbeings.

Ijustlovethem.Iloveeverything thattheyrepresent.Theyrepresent freedomtome Q:Famously,youonlywear black.Telluswhy.

Iknow.I’mtrying.Imaybeswitching that

ImostlywearblackbecauseI’mjust sobusy Decisionfatigueisareal thing.Idon’tliketohaveto coordinateoutfitsorgoshop.

Ifit’swhite,IgetmakeuponitorI spillfoodonit,andthenI’vegotto goshopmoreandspendmore moneyandspendmoretimeandall thosethings.

Soblackisjusteasy Itlaststhe longest.There’snocoordination involved.Ijustlikethecolorblack.

Iusedtohaveinsecurityabout everything Iusedtobeavery insecureperson.Ialwaysfeltthe thinnestinblack,soIwouldwear blackbackintheday.NowIdon’t havethatproblemanymore,butI stillwearblackallthetime Sotherearemultiplereasons. Butthisyear,IthinkI’mgoingtogo backtomynaturalhaircolor,which isbrunette.AndifIgobackto brunette,Ican’twearblack,because it’stoomuchdark.Ican’twearblack allthetime.

SoI’mprobablygoingtohavetoshift toalightercolor.I’mexploringother things. Ultimately,rightnow,it’sjust comfortable.It’swhatI’vealways

done It’sthemostefficientfroma timeandmoneybasis,fromnot havingtohavedecisionfatigueevery day.

Q:Loveit.We’llhavetostay tunedonwhatthewardrobe willlooklikeinthefuture. Lastly,you’reclearlyan outlier.Whydoyouthinkit’s soimportanttoshowup differentlyandtaketheroad lesstraveled?

Becauseifyou’renotyou,then what’sthepointofanyofit?

Ifyoucan’tshowupaswhoyouare, whatmakesyoufeelcomfortablein yourownskin,thenyoucan’tshare yourgiftwiththeworld,andyourob yourselfofyourentirelife.

WhenIwasreallyyoung,Ican’t rememberexactly,butIthinkIwas around10yearsold,Iwrotethis poemanditsaid,“Loveme,loveme not,I’mfinewitheitherway,because ifone’slovedbyall,they’dbeasoul ofgray.”

Tome,ifeverybodylovesyou,how areyouactuallyanybodythat’syou? Thatjustmeansyou’rebeinga chameleontoeveryroomthatyou’re in,tryingtobeapleaser.You disconnectfromyourself,andthat’s whatcausesdepressionandanxiety andpeoplebeinglostandunhappy.

Ihatehumansuffering Iabsolutely hateit.Idon’twanttoseepeople suffer.Peopleprobablytrytofitinso theydon’tsuffer,butIthinkitcauses moresufferingthananything.

Whenyoucanaccept,justlikea president,they’renotlovedby everybody.Never.There’sneverbeen apresidentthateverybodylovesthat reallywins Usuallyhalfthepeople don’tlikethemandhalfthepeople lovethembecausetheyactually standforsomething.

That’swhatIbelievetoo Iwantto standforthethingsIstandforand betruetothethingsIstandfor.

SometimesthosethingsshiftasI evolveorasIchangeorasIlearn moreinformationorhavenew experiences.I’vetransformedso muchinmylife,andthat’sokay.You don’thavetostaythesameforever.

Butshowingupasyourauthentic selfissofreeing.

IrememberIusedtobedeeply insecure Myoldestbrotherwasvery hardonmefromaveryyoungage. Hemadefunofme.Hewasvery tough.MyideaofmyselfwasthatI wasaworthless,uglypieceofcrap thatdidn’tbelonganywhere,to anyone.

Thatstemmedintoalotofissues growingup.

IrememberwhenIwas18yearsold,I gotanosejobbecausehewould makefunofme,andIfeltlikeI neededtolookprettierorwhatever, andsocialmediawasathingandall thesethings.

Igotanosejob,andIremember feelingterrified Thiswasalongtime ago.I’mturning30inApril.

Iwas18andIstarteddatingthisguy, andIhadn’ttoldhimthatIgota nosejob Ihadthisdeep-rootedfear NowIhavepicturesonmywebsite ofmegrowingupandthroughout mychildhoodandallthatstuff,but atthetime,Ihadthisdeep-rooted fearbecauseIfeltIwasnotenough I feltthatIwasnotlovable,thatIwas unworthy.

AllofthatpainIwasfeelingwasfrom me,becausewhenItoldhim,hewas like,“Idon’tcare.Youwerebeautiful thenandyou’rebeautifulnow.Why wouldthatbotheryou?Why wouldn’tyoutellme?”

SoIwascreatingthepainwithin myself.

AssoonasIletoutthesecretthatI thoughtwasmysecret,itnolonger botheredme.Itnolongerhadany weightonme.

know your secrets are what cause your pain, the rest of the world doesn’t even care.

And if they do, it doesn’t affect you because you don’t care. All that really matters in how we feel is how we feel about ourselves If somebody’s opinion of you upsets you, it’s because you feel that way about yourself.

When I finally started to learn compassion and love for who I was, and could be honest about all my fears, all my anxieties, all my faults, all my everything, then everybody else’s opinion no longer mattered one bit to me, because my opinion of me was high. My confidence was high. That no longer had power over me.

I’ve felt the pain of needing the approval of everybody else. Ultimately, it comes back to: we have to have the approval of ourselves

As long as we don’t have the approval of ourselves, we will live in a prison for as long as we live. We will be inauthentic We will not show up ourselves because we do not love ourselves internally.

That’s where all the inner work comes in, and that was the journey to get to that place of self-love.

Whenyoucanshowupyour authenticself,whenyoucanbe honestandtruthful,andwhenyou

But now I love myself. I really truly do Whether this person disagrees

withmeornot,itdoesn’taffectme onebit.Itdoesn’taffectmygreen zoneonebitbecauseIknowwhoI am.

Ilovedifferentperspectives I’m totallyopentodifferentperspectives, evenangrypeople,becauseIknow angrypeoplealsodon’tlove themselves.

Ifsomebody’sgoingoutandtelling youhowstupidyouare,orhowugly youare,orhowincapableyouare,it’s notaboutyou.It’saboutthem.They thinkthey’restupidanduglyand incapable.

Thatwasthebigthing.Being authenticallowsyoutotrulybefree. Ifyou’renotauthentic,Idon’tknow howonecouldtrulybefree.

Andifyou’renottrulyfree,youreally can’thavethegreatestlife.

JACOB COHEN with...

Elite Endurance Athlete, 5K Specialist, Relentless PaceSetter, and Student of Mental Grit.

Q:YouwereaDean’sList BusinessstudentatGeorgia State.Whatdidyouthinkyour careerpathwasgoingtobe backintheday?

IthoughtIwasgoingtobe well,I amrightnow sittinginan investmentbankingjob Iworkedat theNewYorkStockExchange,and thenIwentintoinvestmentbanking. AndIwaslike,“ThisiswhatIwantto do.Thisistheidealworld.”A successful,almostpretentiousjob,at leastthat’swhatitfeltlikeatthetime. Andthat’skindofwhatIwanted.

ButthenthingschangedandIgrew up,Ithink Irealizedthatmoney’snot everything,andrealizedIwassuper intofitness,superintohealth.Isawa lotofmyfriendstakingthisfulltime, andIwasinspired.

Q:Whenyouwere24,you weren’texactlylivingthe healthylifeoftheathletethat weknowtoday.Sotellus whereyouwereatbackthen at24versuswhereyou’reat today.

Yeah, I was 24 I was probably 50 pounds heavier than I am right now, and was drinking, was smoking, was taking Xanax, was taking Adderall, was taking a lot of drugs, and not happy, not fulfilled. I was essentially living an unfulfilling life, working long hours, and yeah, wasn’t really happy.

Q:Andwhathasthat transformationbeenlike?

It’sbeengreat Iactuallygotaskedin anotherinterviewearlierthisweek, doIregretanything?Andtheanswer isno.Ithinkwhatshapedmeiswhy I’mthepersonIamtoday The transformation’sbeenpretty remarkable.

Alotofpeopleask,“Youdiddrugs? Didyouhaveadownloworworst bottomoutmoment?”Andthe answerisno.Itwasacombinationof alotofmoments.Therewasnoone thingthatledmetothis transformation Itwasstartingtobuilddailyhabits. Startingtogotothegym.Probably stilldoingdrugs,butgoingtothe gym.That’sagoodstart.Andthenit justcompounded Eatinghealthier, running,allthesethings,gettingoff drugs,andthenallofasuddenI’m running60milesaweek,notdoing thedrugsIhadbeendoing,livinga happierlife,morefriends,more freedom,beingsuccessfulatmyjob.

Soit’sreallyjustacombinationofa lotofdailyhabitsthatIstilladdtoand trytoadd Idon’tdoallofthem,but it’salwaysaworkinprogress.

Q:Youhavecompletelyblown uponsocialmedia.Youwent fromprobablynexttonothing

totodayyou’veprettyquickly amassed,asofthisrecording, over150,000followerson Instagramalone.You’ve pledgedtodoa5Keveryday inanefforttogettoaquarter ofamillionfollowersbyMarch 1st.Whatwasthemoment whereyoudecidedyouwere goingtobethe5Kguy?

IthinkwhenIlookback,themoment Idecided andthere’sabig backstorywecangetintolater essentiallywhathappenedwas:alot ofthisstardomandstufflikethat,not tosayI’mastar,butalotofthisstuff isn’tjustanovernight“Howdoyoudo that?”

Istartedpostingcontentoverayear agoeverysingleday.Iwouldpost everysingleday.Iwouldpostday-inthe-lifevideosSoIgotveryfamiliar withthecamera AtfirstIwasnot AndIwasconsistent,andthatwas kindoftheonethingthat’sledmeto whereIam.

Ninety-one days ago, I decided to embark on this challenge because I thought it would be a unique opportunity. I thought it’d be good entertainment, and I thought it would make people laugh and be a more relatable way into fitness

When I started this fitness journey, the only people online were very serious “You have to do this exercise this way, you have to hold it for this amount of seconds, you have to eat this amount of stuff.” And I’m like, “I don’t want to do that. I’m not going to be perfect I’m not going to be some bodybuilder.” That wasn’t my goal.

So looking back now, I’m trying to get back to what brought me here. It’s having fun around fitness. So I started the challenge to have fun and to enjoy fitness and bring a kind of light

After probably a week of doing it, one of the videos did well. The first video did okay After a week, I texted my friends, “I don’t know if I want to do this. This is brutal. This is hard editing. This is a lot.” And they’re like, “Just keep going.” And I kept going.

Probably 15 or 20 days in, I was like, “Okay, this is getting real traction. Real celebrities are reaching out to me This is something” So that’s probably when it dawned on me that the basis for my content is

I don’t want that to always be 5Ks. I like running, I like fitness, I like entertaining people. It’s probably not going to always be 5Ks, but this was a really cool challenge, and that’s where it all started.

Q:Whowasthefirstorthefirst fewpeoplethatcameintoyour feedthatyouwerelike,“Oh myGod,Ican’tbelieveso-andsoisconsumingmycontent”?

ThefirstpersonwasCaseyNeistat.He repostedoneofmyreelsand followedme,andIwaslike,“Oh,I’ve beenwatchinghimandhisYouTube videosforever.”Sothatwaskindof surreal.

Fromthereonout,it’sjustbeen running 5Ks.

Everydayissomethingnew.New peoplearereachingout,newpeople arefollowingme Ican’tevenreally keepupanymore,whichisgreat.

Butyeah,thatwaskindofthestart. AndthenIgotinvitedtoDavid Dobrik’shouse,heisanothercontent creatorI’vebeenfollowingforever. Kindofgrewupwatchinghim.So thatwasareallycoolcollab experience.

Butultimately,CaseyNeistatwas kindofthefirstonetobelike,“Oh, thisisreachingpeople,”whichis crazytothink.

That’sagreatquestionbecauseIask nonstop.

myselfthateveryday,andthenI figureoutsomethingtodo.

It’sreallynotabouttheideas The ideascome,especiallynow,viaDMs.I usuallyjustsitandthink,andthat processinvolvescomingupwith lists,comingupwithfunthings,and moreentertainment

NowI’velearnedthroughthis experiencethatpeoplelike claustrophobicspaces,peoplelike tightareas,andpeoplelikeseeing mesuffer.That’swhattheinternet viewsasgoodcontent.

Q:YoumentionedDavid Dobrik.SoDavidDobrik,for thosewhodon’tknow,has9.5 millionfollowersonInstagram alone.Andyoudida5Konhis bedwhilehewasediting,I think,ablog.Butyouhave donesomeofthecraziest5Ks imaginable.You’vedoneone runningaroundatoiletseat. Youdidoneonthetopofyour refrigerator.Youwent througharevolvingdooruntil youhita5K.Howdoyou comeupwiththeseideas?

Sowiththat,Iwilldrivearound sometimesthroughthecityandjust think,“Oh,that’sagoodspot.”Other timesmyfriendswillrecommend stuff.OthertimesI’llgetinspiration fromonlineorwatchingmyold videos That’sreallyit.Takingthementality ofaMrBeast,kindofaDavidDobrik figure,becauseIthinkthisexpandsa lotpastrunning Althoughthat’s whatIamandwhatIdo runandlift andtrytobeashealthyaspossible theentertainmentsideisreally interestingtome.

Sothat’showIperceivethings.Ilook atotherpeople’scontent.Ianalyze JakePaul’scontent,oldstufflike that.Alotofpeoplearelike,“How’d youblowupsofast?”Andthere’sa lotofbehind-the-scenesstuffin

termsofanalyticsandveryspecific things.

Yes,consistencyisnumberone,but it’salsoalearningprocess Idon’t knowanythingaboutsocialmedia.I stillreallydon’t.ButI’mlearning everyday.

NowpeopleareDM-ingmeevery day,commentingeverydaylike, “Hey,youshoulddoonehere,”or “Youshoulddooneinhighheels,”or “YoushoulddooneX,Y,Z.”AndI’m like,“Okay,maybeI’lladdthattothe list.”

SoIhaveanongoinglistofalotof places.Somearemoreeasily accessible IhavetheWhiteHouse onthere.Ihaverunningaroundthe pyramidsinEgypt.Ihavesome crazieronesandsomemoredoable ones.

I’verealizedthishasgottenmeout ofmybubbleshell.There’sstuff whereIthink,“Idon’twanttodothat today,”butthenIgodoitbecauseI setupthischallengeandforced myselfoutofmycomfortzone.And thenIthink,“Whoa,thatwasthe bestthingIcouldhavedone.”

BeforegoingtoDavidDobrik’s house,Iwaslike,“Ireallydon’tneed togooverthere.”It’salongflight.I wasgoingtoLAforaday.Butit pushedmeoutofmycomfortzone

andpushedmetonewlimits,which Ilove.

Q:Whatarethemaybetwoor threethatyouwerelike,“Oh myGod,neveragain,”and thenacouplethatwerereally enjoyable? IwillsayIwillprobablyneverdoone onmyfridgeagain Thatwasjusta pain Iwillneverdoone

Q:So,describetopeoplehow youdida5Kontopofa refrigerator.

Letmeun-blurmyvideorealquick There’sthefridgerightthere.Sothat wasthefridge.Igotupinthatcorner andIspunaround.That’showIdidit. Ihadmyfriendhereonthecouch

Weweretalkingprettymuchthe wholetime.That’susuallyhowIget throughalotofthese.

Q:Howlongdidittake?

Maybeanhourplus Idon’t rememberexactlywhatthetime was,butitwaslongenoughwhereI said,“I’llneverdothatagain.”

Andearlieron,Ithinkthatwasoneof theonesearlieron,Iwasnewtothis contentthing,soIwasn’tgoodat gettingangles.Iwasn’tgoodat…I don’teventhinkthevideowas centered.Idon’teventhinkIwasin themiddleoftheshot Soit’sa learningprocess.

Thatwasonethatwascrazy,andI won’tdoitagain.

TheotheroneisIwillneverdoone onaskateboardagain.Ijustdidthat one.Itdidn’tlookthatbadon camera.Itwasreallybad.Ialmost blastedmyfacewiththeskateboard Thatwasreallydumb.Iwaswalking ontheskateboardandIkepton fallingand…yeah,thatwasnotgood.

ProbablyanotheroneIwouldn’tdo isIdidoneinmywashingmachine, justmovingmyfeet.AndwhenIlook backatthevideo,itwassodumb.So manypeoplecommented,like,“Hey, that’slikea2,000-poundwashing machineandyou’rejustleaningonit oneway,youcouldhavedied.”

SothoseareonesIprobablyshould havethoughtaboutmore ButIdid them,andIwillneverdothemagain.

WATCH THIS NEXT PART!

Because you talk about this quite a bit, why is it important that people take fitness less seriously? And you don’t mean taking your physical health less seriously. It’s the serious nature of people’s demeanor towards fitness.

Tune in to Scott and Jacob’s conversation about this question here:

Q:Whoinspiresyou?

It’satoughquestion.Ithinkpeople likeMrBeast Hetookcontenttoa differentlevelintermsof entertainment,intermsofbrand deals,intermsof,youknow,he’son Netflixnow.He’sgothisownfood company Sopeoplelikethat,that breakbarriers.

People who do not take traditional paths. I see you have Jesse [Itzler] back there behind you. People like that. Devon [Levesque]’s up there.

I was DM’ing with Devon the other day. I’m like, “Dude, you have inspired me because you showed me this doesn’t have to be some perfect, serious route You can have fun” Devon’s out there riding horses, doing whatever he wants, and he’s successful.

A lot of people, I think over the last probably 20 years this has changed, but probably in the ’90s, you didn’t have a lot of Devon figures. And if you did, they weren’t being shown because it was, you know, corporate job, work this, do this. This is how you’re successful. You have a job for 40 years You’re married and have kids by 25. That’s the ideal life.

People who break these boundaries are inspiring. So I get inspired every day

In terms of north star people, I think MrBeast is one. I think Devon is a big one as well, the fitness side of things and kind of the entrepreneurial side. So I would say those two.

Q:Isthe5Kadayabridgeto somethingbigger?Andisthat aclearvisionforyou,orare youfiguringitoutasyougo?

Yes,itisabridgetosomething biggerandbetter.Ihavenoclue whatI’mdoing.Ihavenocluewhat I’mdoingwiththe5Kseveryday.I literallydon’tknowwhereI’m runningtomorrow Ididn’tknow whereIwasrunningthismorning.

IwenttothegymandIthought,“I’m goingtorunonsomekindofpiece ofgymequipment”IdidJacob’s Ladder.

Butno,it’sabridgetosomething bigger Iwanttoentertain Iwant peopletoseemyfitnesslifestyle.I thinkthat’sveryimportant.Butin termsofwheretogo,Ihavenoclue. I’mspeakingwithacontent strategist Thatmighthelpme I thinkit’sprobablygoingtobe somethingalongthelines andI saythisnowandI’mgoingtolook backinsixmonthsandsay,“That wascompletelywrong” butit’s somewherealongthelinesofmaybe Cars&Coffee-ish/runningvibe.That’s whatI’mthinking.

Andifyouaskedmethisquestionsix monthsago,Iwouldhavenotsaid, “5Ksonmyfridge.”SoIhavenoclue wherethingsaregoingtogo,but that’spartofthefun,figuringitout. Figuringoutnotonlywhatkindof contentIliketocreate,butwhat otherpeopleliketoconsume.

Ithinkthat’sabigbalance.Youcan makeviralvideosprettyquickly,but howenjoyablearetheytoyou?In someofthe5KsI’vedone,I’mlike, “Thatisnotenjoyable.Idonotwant todothatagain.”SoI’veshiedaway fromsomeofthose Thishasbeensooverwhelming,ina goodway,thismassivefollowing,but I’veprobablytakenmyfootoffthe gasintermsofmyfitness,atleast running-wise I’mrunningalotless nowbecauseIhavetoeditvideos andI’mdoingthe5K.Iusedtorun 60-plusmilesaweek,trainingfor

stuff.

Today,IsignedupfortheAtlanta Public’smarathoninamonth.Idon’t knowifI’mgoingtotrainforthat.I thinkI’llbedoingLAinMarch.

Soyeah,Ithinkit’smoremarathons, morefitness,havingmebehealthy butalsoinspiringothersiswhatI’m goingtoputattheforefronthere. ButIhavenocluewhereit’sgoingto go.

Q:Hasthisbecomework,oris itstillfun?

It’sfun.Butitiswork.

Editingvideosisnotthemost delightfulthingintheworld.So that’sadifficultquestion.Thereis workinvolved,butI’mhavingfun doingit

Ithink,withanything,peoplehave thisfalsesenseof,hey,ifitstops beingfunandit’swork,thenthat’s notgood Butinreality,alotof thingsrequiresomecapacityof work.

Whetherthatbeyouhavingyour podcastandyou’relike,“Ilovethe podcast,butnowIhavetoemail guestsandsetupbookings,”Not everythingisjusteasy.

Iwantpeopletoknowthatbefore theyembarkonwhateverjourney theywanttodo.Butitisrewarding, itisfun,anditisfulfilling.

Witheverythingdoescomework So I’mverycarefulofthatworkword becauseIthinkthere’sstuffinthe backgroundalways,whateveryou do.

LevesquetoJesseItzler.The commondenominatoris they’realloutliers.They’reall okayshowingupdifferently, andthey’reallokaytakingthe roadlesstraveled.Whatdoes beinganoutliermeantoyou?

Ithinkyousaidsomethingreally importantthere They’reallshowing upforsomethingalittlebit differently,buttheimportantthingis they’reallshowingup,right?

AndIthinkconsistencyisprobably thenumberonethingofbeingan outlier.Anythingyoudo,evenifyou workacorporatejobandyou’relike, “I’mgoingtobethebestlifterinthe gym,”youcandothat It’sjust consistency.

Whatitmeanstomeisreallytaking aroadofmyownjourney.Peopleput onthisstuffthatyouhavetodothis, andnobodydidthattome.

Theysaid,“Youcandowhateveryou want.”Butstill,socialnorms,social pressureon,like,“Oh,okay,I’mgoing todofinance.That’sasaferoute.I’m goingtodoinvestmentbanking That’sahigh-payingjob.That’swhat youwant.”

Andultimately,that’sallstuffthat I’veheard,notstuffthatI’ve experienced.Ihaven’tdonethis.

SoIthinkbeinganoutlierisreally beingconsistentandconsistently thinkingforyourself,consistently beingdifferent.ButIthinkitall comesdowntoconsistencyin whateveryoudowillmakeyouan outlier.

PhotoCredit:LisaBousquet

COVER STORY WITH RYAN LEAF

“You are the sum of all life’s parts. You are not this three-year window of your life.”

-Ryan Leaf

For years, his name was synonymous with unrealized potential and public failure. Drafted as one of the top picks in the NFL, he was expected to become a franchise-defining quarterback. Instead, his career unraveled under the weight of pressure, ego, and addiction, and the headlines followed him long after the stadium lights dimmed.

But what makes a black sheep isn’t the fall. It’s what happens after. In the years that followed, he faced consequences most would avoid at all costs: prison time, public humiliation, and the long, painful work of recovery. Rather than rewrite his past, he chose to confront it, and in doing so, began building something far more meaningful than a highlight reel.

Today, he speaks openly about addiction, accountability, and redemption. In this conversation, he reflects on failure, forgiveness, and the unexpected freedom that comes when you stop trying to live up to someone else’s narrative, and finally step into your own

- Scott MacGregor

Take us back to 1997, ’98, your breakout junior season at Washington State. You took them to their first Rose Bowl in 67 years, where you almost upset the number one team in the country, Michigan. You set a Pac-10 record for touchdown passes and were a finalist for the most prestigious award in football, the Heisman Trophy, along with future Hall of Famers Peyton Manning, Charles Woodson, and Randy Moss. The sports world at the time was divided in a heated debate over who should be drafted number one, you or Peyton Manning. Where were you mentally, physically, spiritually at that time in your life?

Ryan: During that final season, I was as locked in as you could be mentally Physically, I felt like the best version of my physical self playing the position Spiritually, I was doing some more things with the sports psychologist at Washington State that helped me get recentered each week, but it was more around fundamentals and technique and visualization.

It wasn’t necessarily my spirituality, which I think benefited because we were trying to do something as a team. When the season was over, or maybe even after the Heisman Trophy and leading into the Rose Bowl, you could kinda see a shift in my personality For the longest time, I thought I was hot shit, but now the world was also contributing and saying, “Yeah, he is He’s pretty amazing ”

When the draft came, whether or not I

was going to be first or second didn’t really matter. In fact, we probably preferred to be the second pick because it allowed for me to go to San Diego and not the middle of the Midwest We also probably weren’t thinking the same things that you should be thinking around who is on that roster They had Marshall Faulk They had Marvin Harrison I clearly thought no matter where I went and played, I’d play well, so why not go to the best possible place you could? And that’s sunny San Diego. So we were looking toward that.

At this point, I wasn’t great mentally, wasn’t great physically when the season was over. I did a lot of celebrating, picked up a lot of awards, and had to get back in shape for the Pro Day. Come the draft, I was locked in again It’s cyclical in terms of season and off-season, and everything like that When I was drafted, I thought, “Yeah, this is about right ”

Photocredit:RyanLeaf’sInstagram

A lot of people ask me about it, “How did you deal with all that pressure?” I said, “No. When you’re drafted that high, when you believe it, you believe, ‘I belong here, and I’m going to go out and play well. I’m going to go out and play great.’” There was no pressure on me, so I don’t ever use that as an excuse. The pressure comes at a later point if and when you don’t perform at the level that you expected and others expected Then the outside noise and criticism start to come

How do you deal with that? How do you push that away? Clearly, I was not good at that part I found it really difficult at the next level for things not to be compartmentalized like they were in college. Everything was in the facility. My coach, my trainer, my sports psychologist. It just wasn’t the same at the NFL level. You were, at 21, supposed to be the leader of men in their 30s who had kids at home. It was a shocking development that I still thought I could play my way through

No matter what had ever occurred in my life, poor behavior, bad attitude, a bad game, I was always so talented and so good, and I worked so hard that I would just go out and play well the next week This would be the first time where that didn’t happen because you’re going up against the best defenses in the world. If you’re not functioning on the highest possible level mentally, spiritually, physically, you are not going to be successful at that level.

This is a short question but it’s a big question, so looking back at your NFL career, what do you think happened in retrospect?

Ryan: I think I just didn’t know how to deal with failure the right way Everybody fails The idea that I didn’t or I hadn’t up to that point is ludicrous to think that that was the case. But then doing it on such a platform, such a level that everybody got to see, it was humiliating and it was embarrassing.

If I would have had the mindset around, “Okay, this is your welcome-to-the-NFL moment. This is where you struggle. This is where you overcome And then you come out the other side,” instead, I kind of got defensive and was backed into a corner, and I dealt with things the way I’d always dealt with them When you’re in a small town or at a small university, you can kind of impose your will on other people, and they cave to it because there really isn’t much backlash outside of where you were at.

There was a satellite truck from a local news station that followed me around, parked outside my house in San Diego I didn’t fully understand the scope of what the media scrutiny was like at the NFL level Then I came to resent it “I don’t want anybody to know my business,” and, “It’s none of your business,” and, “Who the hell are you?” Everything and anything that I could do wrong that may be cliché now these days, when I look back on it, I just go, “What was I thinking?” I did not have the fully developed brain at 21 years old, given $33 million and told I was going to be the leader of this Fortune 500 company.

It’s absurd Then me not utilizing the assets and support available to someone like me in that position, I would have gone about it a completely different way Money, power, and prestige was really a hypnotic thing It lured me in I did not believe that money was going to change me, growing up where I grew up, in the family that I did.

I was just so absolutely insecure when it came outside of football. If there was anything critical of me outside of the game of football, and when it became the game of football, which I was always good at, which I could always self-correct with, that’s where I believe all my troubles happened It wasn’t because I wasn’t talented I was one of the most talented athletes that had ever come out in the NFL draft

Peyton threw more interceptions our rookie year than any rookie had ever had. The idea of me doing that and how embarrassing that would have been to me in comparison to Peyton and how he viewed it, how he saw failure as an opportunity to do it better the next time. It was all about what your mentals were telling you and how you effectively changed what your optics were It sucks that eventually I came to understand and know these things, but at the time when I was the most talented at what I could do, to play at a higher level and to succeed at that, that’s disappointing

I’m really grateful for everything that happened because of where I’m at now, but I’m also seeing these individuals like Maxx Crosby, Darren Waller, who figured it out in their prime of playing and now get to be the best possible person, human being, version of themselves, as well as that elite football player at the highest level at their position

I think that’s incredible I’m really proud of them and excited for them I suppose those would be probably the easiest people to be resentful of, but there’s just no reason for that I want guys to be successful and find their way in a way where I didn’t.

Photocredit:RyanLeaf’sInstagram

Let’s talk about the B word. I’m sure at some point you thought that “bust” would be attributed to your bust being displayed in the Hall of Fame in Canton and not associated with failure. What’s helped you take the power away from that label, which I think could be crippling for a lot of people?

Ryan: I didn’t know that the statues in Canton were called busts. I don’t think I’d ever heard that word associated with a failure at the NFL level either. It just wasn’t a word that I knew.

When the word started being used a couple years into my career, I didn’t quite understand it. I also didn’t fathom that it would have such an effect on me It’s so silly how somebody who goes to the NFL from a small town in Montana could ever wholly be seen as that to anybody

That’s more of a projection from everybody else who uses that word than it ever is for me, because the expectations that I had were more than any other person could have had for me There’s no person out there that had higher expectations for me than I did

That word should not really have held any merit, but it did because it got used consistently I was so worried about when I walked away from the game, the judgment, the fear, all the insecurities that go along with being a flawed human being, I think is what was there.

How I’ve taken it back? I understand and know that it’s utter BS. It’s a projection of someone else not liking the fact that I should have been better at what I did and didn’t accomplish that, so that pisses them off ‘cause they’re jealous of it

A way for me taking power back is I just talk about it I talk about what I went through My podcast is called BUST: The Ryan Leaf Story It’s me and ten episodes in front of a microphone just telling my story.

When you talk about it, when you own things, when you take accountability for the shortcomings you have and what you could have done better, and accept that it’s a reality, that takes away the power If somebody ran up to me on the street and looked at me and said, “You bust,” I would literally start to laugh because I’d think, “What’s wrong with this person, and can we help him or her in any way?”

I walk through these doors and I see these kids and my family and everything like that, and I go, everything I have is

because of my mindset and the fact that I got to play football for a living It’s given me everything, so how could that ever be a negative?

It’s amazing how much the game of football has given me and continues to give me Ironically enough, maybe if I was middle of the road, played a couple years, no one ever heard about me or talked about me again, I would not have the life that I have now.

So there's gratitude in that too. There’s almost a thankfulness to the fact that it played out the way it did. You have to come to that point anyway, a realization that you have to be grateful for what’s transpired in your life if you’re still here If you’re still here standing and still going through the process, you better be incredibly grateful for what’s transpired and what you’ve been able to overcome and go through

It could be helpful for a lot of people. How do you stay focused on the future when the world and people so consistently want you to look in the rearview mirror?

Ryan: For me, that’s probably from my recovery world I don’t look to the future either I don't look at the future at all I don’t look more than a day into my calendar for what’s next It’s a day-at-atime thing Sometimes breathing, 60 seconds at a time

I can’t control what you think of me or what happened 10 minutes ago. I can’t change that. If I made a mistake, I can make amends for it and we can move forward. Whether you forgive me or not, that’s up to you. That’s another thing I

I can’t control

That is the antithesis of living in the present, being where your feet are at all times, and remembering that you can only control your attitude, your behavior, and your effort That’s it You can’t control what somebody else thinks or what you did in 1997, 1998. You can’t control any of that stuff.

All you can do is control you now, and that seems to have really worked for me, especially over the last 13 years. It’s been a slow climb to get to that place. Ironically, I’m more confident as a human being now with all the baggage and all the scars and everything than I ever was as a starting NFL quarterback

I think that leads to the idea that you are the sum of all life’s parts You are not this three-year window of your life It may be the way that other people want to compartmentalize your life, but if I plan to live to 90, it’s going to be an absolutely minuscule speck in my life.

That’s important to remember. That’s mental conditioning. That’s continuously using affirmations in the mirror, like, “What other people think of me is none of my business.” At the beginning, that was really difficult to say because it was so much of my business what other people thought.

Now I believe it. When I wake up in the morning and I say it to myself in the mirror, it’s a belief. You train your brain like you train your body Same thing It takes time, but you get to a place where I don’t care what you think of me That is none of my business, and it sounds like that’s a you problem and not a me one Those are little things that I continue to reference If people like to bring it up, I’m very good at being self-deprecating, owning my stuff, and owning them from time to time.

December 3rd, 2014, you’re released from prison, and during that time, helping inmates learn to read became, I think, kind of a lifeline for you. What did that experience of serving other people mean to you?

Ryan: I didn’t want to do it. I was really okay with just sitting on my butt, getting fat, watching TV, and ultimately just kind of dying. I think the irony in all this is somebody who could be so mentally tough can get to a place where they’re so mentally vulnerable. It’s hard to imagine that’s where you get to, but that’s what addiction and mental illness does It tricks you into believing that you have to do this alone, that you aren’t mentally strong There’s a weakness that’s been attributed to it for so long because of stigma That’s the place I was in

I wasn’t looking for anything, and luckily for me, like had happened in the past during the process, March 30th, 2012, the sheriff’s department showed up and they saved my life It was my higher power saying, “You can’t do this on your own, Ryan. We’re going to have somebody come help you.” You don’t see the sheriff’s department as a guardian angel at the time, but retrospectively you look back and see they saved my life that night. Where was I headed? What was I going to do? When my reality wouldn’t shift while I was in there, my higher power sent my roommate He was an Afghan-Iraqi War vet, and he convinced me one day that I should get my head out of the sand and understand the value that I had, not only for the men in there but for when I got out

He said, “Ryan, you’re going to get out at some point.” I kept pushing that off. I kept denying my parole. There was something about being in a prison where I would never welcome it back now because I know what I have, but at the time I was like, “This is heaven. I don’t have to do anything. There’s no responsibility. I’m not messing up people’s lives ” It was a selfish way to look at it because no family wants their loved one in a prison cell But I was okay with that

He suggested we go do that, and I still remember going begrudgingly I remember what it felt like I was metaphorically kicking rocks as I walked down the prison hallway thinking, “This is stupid. This isn’t going to help me. Doesn’t he know how important I am?” Therein lay the problem. The guy in a red jumpsuit in a prison hallway still thought he was important.

There’s a fine line of having self-worth and being an egomaniac with a selfesteem problem I walked into this room and a Native American man, probably mid-60s, came up to me and said, “I never learned how to read. I’ve been faking it my whole life. Can you help me?” This guy had been in and out of prison his whole life, and in a place where you’re not supposed to show that kind of vulnerability and transparency, he did.

That leads to the larger problem of stigma around mental illness, substance use disorder, around anything that you feel like you could be judged on If you can’t read, people say you’re stupid If you’re a drug addict, people think you chose that If you have a mental health disorder, they say you’re crazy That’s what stigma has done over time.

Growing up in the cowboy culture of Montana, I’d never seen another man ask for help. In locker rooms in college and the NFL, same thing. No peer had ever stood up in the locker room and said, “I’m really struggling here, everybody. Can you help me?” If you hadn’t seen it in movies, on TV, or in books, how are you supposed to do it?

And so my first reaction was kind of like, “What’s wrong with this guy?” Then we went to work No one saw it It was these two guys in an incredibly adverse situation, being imprisoned, helping each other. I want people to understand that when you help somebody else and you’re of service to somebody else, they’re doing you a service. It’s reciprocal. Completely.

That’s where it started. You don’t know it’s happening I didn’t think it was anything big I just knew I was going back Months passed, and I realized I was sleeping better, I was more personable, and I was talking to my family Those were three things I hadn’t done in probably a decade I became the TA for the substance use disorder counselor

When I walked out on December 3rd, 2014, I knew it was going to have to be the foundation of who I was or nothing was going to change. I was going to be right back there, most likely dead. That’s where it started. The idea of grateful servitude to others started there. I didn’t know what was happening at the time and probably didn’t realize it even when I walked out of prison, but it established a semblance of hope in me for when I did walk out, because immediately I was going to be slapped in the face over and over again with “You’re not worthy,” all these things, the judgment, the fear, all that stuff comes back.

It had to take root at some point, and it had to be about other people and never about myself again. That’s what I’ve tried to make it be over the last decade or so.

WATCH THIS NEXT PART!

Retired at 26, and you'll turn 50 in May, so you're a lifetime away from your playing days, and you look fantastic. What are some of the daily rituals that you practice?

Tune in to Scott and Ryan’s conversation about this question here:

Tell us a little bit about your beautiful family, Anna, McGyver and Bo. Because you light up when you talk about them. Tell us a little bit about them.

Ryan: December 2014, so we’re coming up on 12 years here in December I remember walking out None of that life seemed real, like that could ever be a possibility. There were no job opportunities when I got out. No women

“We believe anyone can be “We believe anyone can be ordinary, but we all have the power ordinary, but we all have the power to choose to be extraordinary.” to choose to be extraordinary.”

wanted to date me. I had a credit score of 500. No one wanted to be around me. You ask anybody at that time if they would have offered me any sort of job opportunity or a date or anything, no, it didn’t exist

That taught me the one step in front of the other, just breathe mentality Six months in, after I got a chance to go down to treatment in Southern California, I walked into a bowling alley that my brother was filming a pilot for Comedy Central for, and in walked this woman.

She’s easy to notice. She’s almost six foot one, brunette, beautiful. It wasn’t hard for me to notice her when she walked in. But I’m a dude that’s six months fresh off a prison sentence How do you approach somebody like that?

She was working that day, and in between shoots, I would approach her and show her the scene if I videotaped something my brother was doing, because she was getting dragged around in the scenes all the time and never really got a chance to see them. So

I showed them to her We got to talking, found out we were both former athletes, and for the first time in my life, I was brutally and openly honest with somebody from the get-go.

Because, listen, you can Google me. You just go home and type my name in and there’s a mugshot that pops up a lot of the time So I told her, “I just got out of prison six months ago ” Later on, she told me it stopped her from Googling me for a while until we had gone out on some dates and she got to know me

So then when she did Google me finally, she would be like, “Oh, that’s wrong, that’s wrong. That's right.” She could filter it. And that all came from being honest and vulnerable, which is not the default setting for us as males to tell women the truth, especially some of our faults and scars.

The rest is history. My brother takes a lot of credit for it, having invited me up to be a part of it that day At the time, I couldn’t afford gas money to get there, so he told me, “Just come watch your brother work I’ll pay for your gas ” I remember at the engagement party, I told my brother, “I never saw any of that gas money, by the way ” He said, “Well, I got you a wife ” He was about right

The night I proposed, we got pregnant. Our journey what we thought it was going to be was that we were going to travel, we were going to just enjoy this relationship that she found later in life and I found much later in life. After a lot of struggles, we were like, “We’re going to travel the world together and we’re just going to have the most fun ” And then we found out we were pregnant

I never thought I wanted to have kids because the old mindset was I don't want to ever saddle anybody with my last name, but how selfish is that? My dad has that last name My grandfather has that last name One's a Vietnam vet, one's a Korean vet, who served our country I mean, what a selfish way to look at things

So I was never really interested in having kids because of that. Also, I was worried kids would make fun of him and stuff like that.

And again, that's very selfish, because he could be the most lovable kid in the world and everybody loves him, and no one would ever make fun of him because of his dad. And so when we found out, I was really excited, and I think she was too, and we delved into and started that world of being a parent

So we kinda had to put our personal relationship goals to the side a little bit And then COVID hit and we were trying to have a second kid and we couldn't She miscarried four times during the pandemic, and it was brutal on her specifically because I can't relate to that. I don't know what to do, how to help, so it was a very hard time, but she was resolute because our son, McGyver, who was our firstborn, wanted a sibling.

She's an only child, I'm the oldest of three, and so we embarked on the IVF side of things, which takes such a mentally strong individual to go through that process of all the injections, all the things that happen and go along with it And at the end, we only came away with three viable embryos

One of them probably was teetering on

not being a viable one. And so we kind of wanted to put the two viable ones in and hope for the best, but our doctor convinced us to put one in, and by a miracle, it took, and Bo Claiborne is her name

Her middle name is Marvel because that doesn't happen And they're six years apart, which ended up being another thing we're grateful for, for the way it played out. Six years apart seems to be a really great big brother mentality for him, and she just looks at him like he hung the moon in everything he does, just follows him around, mimics him, does everything.

Being a dad is the best thing I've ever done So it's the proudest I am of anything But you can screw that up if you don't do the right things when you constantly feel like you're doing the wrong ones

I constantly feel like we're screwing up as parents, but we're getting through it and we're getting through it together. I won't say it's been hard because we met 12 years ago, and when you're in a relationship with an eight year old and a two year old, you become like these micromanaging managers of these two egomaniac sports stars or something like that. Taking them to this, taking them to that. Scheduling this, scheduling that. Finding time for one another is incredibly important, and I think the best thing about it is she ended up being my best friend And I've never been able to, in my whole life, been able to tell anybody everything Like, everything

What it’s allowed for is for me to be more open and honest publicly. She’s talked about this, and I have too that we’ve

kind of built our house out of glass. And that removes power. It removes power from anything anybody wants to hold against us or say about us, because we’ve already done it

We've already said it You've seen it This is our life You don't like it? Too bad We love it We're going to continue living this way and doing this the way we want to And it doesn't mean we don't screw up, but when we do, we're open and honest about it.

I think it's ended up making us more relatable. And I love her for it, because she did not need or want to go necessarily on this journey with someone like me, and she has. She's an incredible partner and incredible mother, and I know it's weird to look 16 years ahead when the baby girl heads off to college, but we're looking forward to our retirement in Northern California

You have a ton of irons in the fire professionally. Tell everybody what you're working on now and what do you see in the future?

Ryan: Like I talked to you about, there was nothing when I walked out. There was just nothing available to me. You had to start from day one, and initially it had to be service-based, whatever that looked like And one of the best things about being a convicted felon and a drug addict is that sober living houses and recovery movements are always willing to take a look at your resume, even though you've had to check the box for felon

That's where I ventured into first. I

started working with a group called the Transcend Recovery Community in Los Angeles. They had eight to ten homes in the Los Angeles area catering to individuals who are in need of substance use disorder treatment, usually with cooccurring mental health diagnosis

I went to work as a driver at one of the houses, and working as kind of a manager in the house, being a support staff for them. And it paid 15 bucks an hour. I tell people that story all the time, because I was making five million dollars a year at one point and was miserable.

I was miserable as a human, was miserable to be around, and I was just offered this job for $15 an hour, and I felt more value than I'd ever felt before. So it lent itself to the idea of economic wellness versus what was real I know how far a dollar can go now, and I know how important it can be if you're able to make some money

But I know that that's not going to be the answer for your happiness It's most likely, if you aren't in that place, going to expose any sort of character defects. And that's certainly what was the case with me.

So going into this now, and listen, making 15 bucks an hour wasn't like it was all of a sudden getting a signing bonus for $11 5 million again But I remember going and taking a picture of that first paycheck and sending it to my parents, and then when I went and leased my first car, a Kia Hybrid, it was just like what's crazy about renewal and recovery is it's almost like you're starting over There's an innocence to it because you get to start your life over again.

No matter what you felt like you've done wrong in your life, you get this rebirth, if you want it. You can choose how you want to view it But I got to do the things that I got to do over again, things that I should have done out of college when I got my first car, rented my first apartment, or anything like that, where those were these sentinel moments in my life They were overshadowed because I went from bouncing a check at Pizza Hut in March of '98 to being handed a check for $11.5 million.

So this was all new for me and something that I was really reveling in. And so that's where the work started. My boss at the time was a sports fan. He really felt that my story would impact a lot of people because of the notoriety around my football career

And so he suggested we start getting out and maybe speaking to the youth, high school and middle school kids in the local area Now that was kind of the furthest thing that I wanted to do I just wanted to find this peaceful, unchaotic life and disappear. Unfortunately, fortunately now I suppose, my name doesn't disappear.

Every April the draft happens, and when you take six quarterbacks in the draft in the first round a couple years ago, that's what this game's about, the quarterback position So my name gets brought up every year It wasn't going to go away And so I had to figure out a way to take that power back and start using it to my advantage

Otherwise, it would just destroy you, the constant criticism and judgment of something that you have zero control over anymore, and allowing that to affect

you. So I started to go out and speak, and when I started doing that, I found that it became incredibly therapeutic to own your stuff, not give any excuses, and tell people what you've done to organize this change and make it solution-based so someone may have the life that you have now

That's where the speaking started I went to the Super Bowl to get a health check. The NFL offered these brain and body scans at the San Francisco Super Bowl 10 years ago, and while up there, I ran into Executive Producer Paul Pabst, who has been the EP for Dan Patrick for forever.

Paulie was a good friend of mine, and he suggested that I go on the show and tell my story a little bit the next day in San Francisco And I was very hesitant, because most people probably didn't even know I was out of prison I didn't want to be in that public eye for all the judgment parts of it, not understanding that being in the public eye now, for shining a light and being a lighthouse to other people, was now the calling.

And so I went on his show, and it was absolutely a trial by baptism It was just me laying bare to everybody, owning the stuff that I did, and it was incredibly wellreceived. I went onto the radio roll over the next few days. ESPN and E60 reached out with Tom Rinaldi and asked to do a documentary.

I didn't want to do it, and I also told him that I didn't want to do it, but if I did, it would have to be a long piece It would have to be 18 months You'd have to follow me for 18 months We weren't going to do this where you follow me for a week and all of a sudden you go tell a story, and then a year later I'm in jail again for relapsing I said there has to be substance behind this And that's not normally something they do, they don't put that kind of time and effort into following a subject. They want to churn them out, put them on TV, sell the advertising, do all the things like that.

But Tom convinced them to do it, and he invested in it, and we did that for a year and a half And when it finally aired, though I felt like it could be less sportscentric, it affected a lot of people And so that's where all that kind of stemmed from

Nick Saban saw the documentary He invited me to come speak to his team He was the first coach to ever do that, to have me stand in front of a collegiate football team made of a lot of NFL prospects and share my story in a hope to help move them in the right direction. Since that referral from the greatest coach to ever coach college football, I've now spoken to 78 football teams over the years, some duplicated.

Lane Kiffin's had me three times. I don't think Nick Saban understands what an unbelievable referral he became when he just asked me to come and talk after seeing that documentary And it's something I continue to do

So we started a business, my wife and I We started a consulting and production business, and at first it was really small We used it so that we could be paid through that and understand that aspect of things. And over the last 10 years it's actually become a very successful business.

All our productions, we are producers on, whether that's my work with Sirius XM NFL Radio, whether that's my work as an analyst with Westwood One with NFL games, or if it's my work as an analyst with The CW Sports around my TV work Anything we do, we do

All my speaking engagements throughout the country are run through our company My wife is the COO, I'm the CEO, and I didn't anticipate being incredibly savvy at business, but I also married a business graduate from Georgetown University, so I guess I associated myself with good people taking me down that road, and we've built a very strong business.

I would say that our speaking, our consulting aspect of it is probably a large portion, if not 50 to 60% of our income The broadcasting side is allowed for because of the foundation we built around being of service to others, and that allows me to go out and have fun and be this analyst and be back in the world of football

I always thought for a while that the

football part was the toxic thing, not understanding that I was the toxic thing, and no matter where you go, there you are Unless you change the problem, that's always going to be the issue And so now I relish the idea that I probably wasn’t the best person to work with in years past One of my main goals when I go to work on these broadcast crews is that the people I work with because it may be the only time I meet them, whether it’s a cameraman, a runner, or a PA walk away thinking, “He’s a lot of fun to work with.”

That's the only goal I have. I want to do a really good job, don't get me wrong. I work really hard, I study, I plan for what I need to do when I step on air, but when I walk away, I want the people that I worked with to have had such a great time, as I did doing it

That’s been a work mantra for me, and we're just continuing to try to build that We work tirelessly at the work side of things It's nice because we're able to be home with one another to work But listen, that's just a quarter of what she does business-wise.

She is a real estate magnate, man. I married up for this deal, right? She's got properties all over the United States. She manages them, she runs them, she runs our house. Our house is a big deal. We bought a house that was built in 1994, and when you buy it, you love it, and then you realize that pretty much 30 years of wear and tear, you're going to have to almost kind of rebuild it, and she's been doing that with the house

So as much as everybody wants to look at me as an outlier, I think this is more of

a cumulative effort of two outliers that found each other and made this amazing business and everything work

Turning over a new leaf is an old reference to turning a page in a book, but it's used today to symbolize a fresh start and a change for the better. You certainly have done that. What do you hope the next chapter of your life looks like?

Ryan: I work really hard at being good at what I do as a broadcaster I worry sometimes I'm limited to how far I can go because of my history, and that's understandable. There's consequences to your actions. I get that. I can be just fine with whatever level I stay at, because I could call a group of high schoolers out on the asphalt playing seven-on-seven and I would enjoy that.

I'd love to be on television calling the NFL games for CBS or Fox I just don't know if that's ever going to be a reality But then things change My boss at Westwood One gave me my first playoff game this year

Every time I feel like I can't get any further, all of a sudden something remarkable happens, and it allows me to be grateful for it in the moment. But me, as somebody who always has been high achieving and wants to achieve more, kind of gets back into that mode. And so that's a big reason why I don't think too far ahead, because I don't want to get outside myself and living where my feet are right now

Today's schedule was go on this with

Scott and answer the questions as honestly and as wholeheartedly as I could.

Another part of my business is working with treatment centers, and one of them is the Menninger Clinic, which is a stateof-the-art psychiatric and substance use disorder facility down in Houston, Texas. This is my fourth year working with them. Today we have our bi-monthly meeting where we talk about what I can do to help their facility I go down there quarterly to do some work

So that's the day pick up Bo from daycare, when our son gets home do homework with him, get dinner ready and everything like that

I'm not looking too far ahead. I know that next football season will come, but right now it's about keeping our business moving forward, this off-season part after the Super Bowl until the season starts again in August when I go speaking to colleges.

We try to find maybe one event a month

we can do where I'm not away from the family, where I'm home all the time and we're all together doing this thing.

So to answer your question longwindedly, I just want to be the best father and partner that I can be. That's all I care about. If everything went away, if all the work went away, all the jobs, all the money, I know that we'd be fine, because I think the superpower that I was granted through everything I went through is perspective

My perspective allows for me to be living in a constant state of gratitude, because it never can be what it was And any time I hear anybody complain, I can always be like, "Hey man, it could be worse " "How?" "You could be in prison." And that is a constant reminder, and one that immediately shocks you back to the present and understanding how important what you're doing in that moment is.

And so that's the world I live in now. I live in now, not five years from now But doing what I'm doing now propels what five years from now will look like

Incredible, because if you would have told me 10 years ago when I walked out of prison that this would be my life now, I would have told you, "You're nuts You're certifiable. There's no way that is any bit a possibility. Married, two kids, living in your dream house with your dream jobs, that's what's going to be available for you 10 years from now, after what the previous 10 years had looked like as they transpired." I would have said, "You're nuts. That is impossible. There's no evidence to back that up. The evidence that backs it up would be to say that I'll be back in prison or most likely dead "

A lot of times when I’m working with new people, nothing can carry you 18 months

A lot of times when I’m working with new people, nothing can carry you 18 months down the line. You need those 18 months of down the line You need those 18 months of struggle, adversity, overcoming to put struggle, adversity, overcoming to put yourself in the position that you’re going to be 18 months from now, and you’re yourself in the position that you’re going to be 18 months from now, and you’re going to be grateful for that. going to be grateful for that

And so that's where I live. That's the world I live in on a daily basis. And so that's where I live That's the world I live in on a daily basis

FUELFOR FUELFOR YOUR YOUR OUTLIER OUTLIER MINDSET MINDSET

HAND-SELECTED NUGGETS FOR YOUR NOGGIN

BLAH BLAH BLACK SHEEP

N. D. WILSON

“Blah Blah Black Sheep celebrates the courage to stand apart, think differently, and trust your own voice;lessons every outlier learns early It’s a reminder that being the “black sheep” isn’t a flaw; it’s often the beginning of leadership, creatvity, and brave thinking”

OM Staff pick-Scott

STEVE JOBS “THINK DIFFERENT” CAMPAIGN SPEECH

This is a natural fit for our Black Sheep issue because it captures the essence of challenging the status quo and celebrating those who dare to think differently the same spirit that defines every outlier and unconventional thinker we champion.

OM Staff Pick-Kathy

LESSONS FROM TWENTY EXCITING YEARS AS A BLACK SHEEP

DR. DETLEF REIS

“This piece is a lived manifesto for outliers; proof that choosing the harder, truer path demands courage, sacrifice, and resilience It reframes success away from safety and approval, reminding us that meaning, passion, and long-term impact often come from daring to stand apart, be disliked, and keep going anyway.”

OM Staff Pick - Melissa

FEATURE STORY

By: Megan Gross, Founder of The Bon Soir

“Outlier hosts aren’t the ones with “Outlier hosts aren’t the ones with the biggest guest lists. They’re the the biggest guest lists. They’re the ones who do the unscalable work.” ones who do the unscalable work.”

Everyone wants their event to be extraordinary.

But most are afraid to be unconventional. They think the problem is their venue, their keynote speaker, or what's on the menu. But the real problem runs deeper: they're optimizing for the wrong metric entirely Most events are optimized for attendance Outlier events are optimized for relationships I've been hosting events for

nearly two decades, starting in the biggest nightclubs in Vegas, moving to the most exclusive clubs in Paris, and now hosting events for top investors in the heart of the startup ecosystem and the companies that came out of it.

The landscape is changing We have entered the IRL era AI and technology have individualized our world to an extreme degree, and humans simply weren't built to live so separately

In-person events have become our way of bringing ourselves back together. But here's the catch: just like your social media feed feels noisier than ever, the event world does too. The space is more saturated than it's ever been, and the appetite for average has disappeared entirely

Standing out now requires something most hosts aren't willing to do: closing the door, investing in people, and committing to unscalable work.

01 Curate like you are a surgical sniper

Every event promotes “networking”

But what most hosts are really doing is carving out time for serendipity, hoping attendees might stumble onto someone relevant That’s not connection That’s a lottery.

What people actually want is a highly curated room. They want to be in a room with their people. They want opportunity, support, and love reflected back to them. They want to be associated with high-caliber people who are collectively serving a larger purpose

So instead of blasting your event invitations like you're firing a bazooka, spraying invites to anyone with a pulse (or bot), you need to

approach your guest list like a surgical sniper approaches a mission. Give your event one razor-sharp goal: a specific shift or outcome you're trying to achieve.

Not: “I want to meet and connect with other likeminded people”

Instead: “I want to connect with people who identify as outliers, building unconventional careers and companies, so we can do extraordinary stuff with extraordinary people”

And then curate your guest list with the same surgical precision. Every name should serve the purpose. Every invitation should be deliberate.

Here's what most hosts don't realize: when you close the door to those who don't align with your purpose, you're actually being generous to those who do

The biggest mistake people make with their events? Letting everyone in.

02 Tailgate your event

Most hosts think the event starts when people walk through the door

But the event actually starts the moment you send the invitation. The pre-game is where your real strategy lives, and it's also the most underutilized lever you have.

An outlier host pre-games their event as if they were tailgating They get their

carefully invited guests as pumped up as they would be for the big rivalry game.

But in this modern digital age, people are relying on automation tools to do the inviting for them. Then they wonder why attendance is weak. They think offering free food and drinks the bare minimum will be enough to get people to show up You are going to have to work to get people to show up, and when you do, it will pay off big time

To break through the AI noise, you will need to personally invite each guest. Send a text. Pick up the phone. Send snail mail. Heck, if you can send a pigeon post, do it! Put some real elbow grease in and do the work here. This is what stands out, yet this is what most hosts aren't willing to

do And when someone receives a personal invitation instead of a mass blast, it creates an initial touchpoint of trust.

Once people RSVP, use a short intake form to gather data that helps you personalize the experience. If it's a seated dinner, assign seats strategically based on their interests If someone shares something meaningful, bring it up and spark conversation around it It's your duty as the host to keep the conversation going and the connections flowing.

And don't let the event end when people leave. Send a personal thank you note afterward with photos from the night and a hint at what's next. Keep the momentum going

Outlier hosts aren't necessarily the ones with the biggest guest lists. They're the ones who do the unscalable work no one else is willing to do.

03 Sweat the small stuff

Most hosts focus too much on the big logistics the venue, the menu, the photographer then call it done and wonder why their event felt forgettable.

The outlier work lives in the micro-moments, the details most hosts skip because they don't scale and take too much effort. Find out what type of cuisine your honored guest loves, or their favorite bakery, then serve it

Curate the playlist with their favorite songs and time them to play when they'll land Create a personalized photo album with key photos, quotes, and moments from the event to send afterward, so the experience lasts longer than the night itself

And for the love of everything, stop giving people crap with your brand on it and calling it a gift. Swag isn't a gift it's overdone, terrible for the environment, provides little to zero value, and says nothing meaningful about your brand Instead, source gifts from local and meaningful vendors that people will actually use and that make them feel part of a community Don't put your brand on it People are not your billboards.

People will remember your thoughtfulness far longer than they'll remember your logo.

Here's what it comes down to: people like to be invested in. You want to impress? Invest. You want to connect? Invest. Go all in on the details, because trust is built in the details, and you cannot put a price on trust

04 Events

are a vehicle, not the outcome.

Most hosts are chasing profit margins, obsessing over how much they're going to charge to cover their costs and try to make a buck.

But chasing profit margins on an event is like charging your friends for a dinner you invited them to: it misses the point entirely.

Unless you're running an event agency, you shouldn't be focused on profit margins at all Chasing $100per-ticket margins is like running a festival, and festivals are almost impossible to make profitable.

Look at Fyre Festival: a vivid example of what happens when you pour everything into the spectacle instead of the strategy

Events should come out of your relationship budget, not your revenue projections. Building relationships is a long game, and outlier hosts treat them like investment funds Like an investment fund, you don't want to withdraw from it the interest will pay dividends far greater than any withdrawal ever could.

You know that person in your life who only calls when they need something? That's a withdrawal. And you can feel it every single time.

You can’t scale special.

Most hosts think bigger is better.

But, ask yourself: why are there only a limited number of Navy SEALs? They make up less than 1% of the Navy

Special has to be small Scale dilutes it

Simon Sinek said this about leadership. Esther Perel said

it about relationships: life is lived in the small details. The same applies to events. You can't mass-produce intimacy. You can't automate trust. You can't engineer the feeling of being seen.

When events are done authentically, they’re not big They’re intentional They’re curated with precision They are focused on the details

This is why the most valuable relationships don't come from the 2,000-

person conferences They come from the small tables with the thoughtful touches, from the conversations that linger long after the plates are cleared, from the people who dared to go deeper than the surface-level chit chat

Special doesn’t scale. That’s why it’s special.

Next time you're planning an event, ask yourself: Do you want to be part of the 99%? Or do you want to host a Navy SEAL event?

The Moat

Everyone is doing the luxury activations, the F1 experiences, the branded spectacles.

But none of it is special anymore Bigger budgets and flashier venues don’t create connection; they're just creating noise

Outlier hosts understand this They're not chasing attendance, ticket sales, Instagram moments, or packed rooms.

Let me tell you about the most personally influential event I ever threw.

It wasn't the New Year's Eve party in a Las Vegas nightclub with John Legend and Chrissy Teigen ringing in the new year alongside 500 megafans It was a small dinner I hosted shortly after I launched my business

In venture capital, women have historically received a mere 2% of venture

funding I wanted to shift that narrative, even if just in my small corner of the world. So I brought together a highly curated group of women who I thought could benefit from each other: founders, investors, and operators who were building meaningful companies and willing to invest in each other's success I called the dinner The Femme Table

I had been curating this guest list for months, adding names every time I came across someone interesting.

T There was one person in here was one person in particular I was especially particular I was especially excited to invite a serial excited to invite a serial investor who's been written investor who's been written about as a "super angel" about as a "super angel" whose mission is getting whose mission is getting female founders funded. female founders funded

This super angel wasn't able This super angel wasn't able to attend my dinner, but the to attend my dinner, but the invitation opened a channel invitation opened a channel of communication between of communication between us We met up for brunch at us. We met up for brunch at my favorite local spot, and my favorite local spot, and what started as a breakfast what started as a breakfast turned into an ongoing turned into an ongoing relationship Two years later, relationship. Two years later, we've collaborated on we've collaborated on multiple events together, multiple events together, and she's become an and she's become an advisor in my business and advisor in my business and a trusted friend. a trusted friend

Events don't have to be Events don't have to be flashy. They have to be flashy They have to be purposeful and curated. purposeful and curated

The hosts who understand The hosts who understand this are building something this are building something far more valuable than a far more valuable than a packed room They're packed room. They're building trust and building trust and relationships that relationships that compound compound.

Most events are optimized Most events are optimized for attendance. Outlier for attendance Outlier events are optimized for events are optimized for rrelationships. elationships

Which one are you Which one are you building? building?

‘emout(liers)...

Meet the dreamers, the doers, and the visionaries who are living proof that the most extraordinary lives are often built on the foundations of the unconventional.

Support these four incredible outliers who are redefining what it means to truly live an outlier life.

Cole Brauer

Aishwarya Iyer

Jack Ó Rinn

Anton Nootenboom

“Being a black sheep is a badge of honor bestowed upon those who stand out in a monochrome world."

Coco Chanel We don’t get to choose our parents or the circumstances we’re born into... We still get to choose who we are, who we want to be."

RICK RIORDAN

I love being the black sheep of my family now that I know I am the dream of my ancestors. It all makes sense.

BERT HELLINGER

"We

don’t get to choose our parents or the circumstances we’re born into. We can’t change our blood. But it shouldn’t determine our fate. It doesn’t. We still get to choose who we are, who we want to be."

RACHEL

HARRISON, AUTHOR OF BLACK SHEEP

ANTHONY T. HINCKS

PHOTO CREDIT: NEW YORK TIMES PHOTO CREDIT: YORK

OUTLIER OUTLIER POWERHOUSES POWERHOUSES

In each issue, we spotlight legendary figures and inspiring outliers

In each issue, we spotlight legendary figures and inspiring outliers who have been recent guests in The Outlier Project. Get ready for who have been recent guests in The Outlier Project. Get ready for thought-provoking quotes that will ignite your spirit. thought-provoking quotes that will ignite your spirit.

MATTHIASGIRAUD

The Outlier Project Guest - January 6, 2026

Super Frenchie®, Professional Skier & Mountaineer, World Record Holder

SHAWNEEDELANEY

The Outlier Project Guest - January 13, 2026 “ONCEYOU'VEBEENTHROUGH

DAVIDBRIER

The Outlier Project Guest - February 10, 2026 -PALAKPATEL

CEO, Vaillance Group, Keynote Speaker, Board Member, Co-Host of Control Room

International Keynote Speaker, Best-Selling Author of Brand Intervention, Branding & Differentiation Expert, AwardWinning Creative Director "FALLOUTOFLOVEWITH YOURSHIT.THATLOVE AFFAIRISECLIPSINGYOUR JUDGMENTTOBEWHATI CALLPASSIONATELY IMPARTIAL."

“Here's to the crazy ones. The misfits. The rebels. The “Here's to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones troublemakers. The round pegs in the square holes. The ones who see things differently. They're not fond of rules. And they who see things differently. They're not fond of rules. And they have no respect for the status quo. You can quote them, have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing disagree with them, glorify or vilify them. About the only thing Photo

-STEVE JOBS -STEVE JOBS you can't do is ignore them. you can't do is ignore them. Because they change things. Because they change things. They push the human race They push the human race forward. And while some forward. And while some may see them as the crazy may see them as the crazy ones, we see genius. Because ones, we see genius. Because the people who are crazy the people who are crazy enough to think they can enough to think they can change the world, are the change the world, are the ones who do.” ones who do.”

Outlier Magazine Spring 2026 Issue

RYAN LEAF RYAN LEAF

TABLEOFCONTENTS

TABLEOFCONTENTS

OUTLIER

HANNAH HAMMOND with...

JACOB COHEN with...

Q:Howlongdidittake?

WATCH THIS NEXT PART!

COVER STORY WITH RYAN LEAF

WATCH THIS NEXT PART!

FUELFOR FUELFOR YOUR YOUR OUTLIER OUTLIER MINDSET MINDSET

BLAH BLAH BLACK SHEEP

STEVE JOBS “THINK DIFFERENT” CAMPAIGN SPEECH

OM Staff Pick-Kathy

LESSONS FROM TWENTY EXCITING YEARS AS A BLACK SHEEP

DR. DETLEF REIS

FEATURE STORY

01

Curate like you are a surgical sniper

02

Tailgate your event

03

Sweat the small stuff

04 Events

You can’t scale special.

The Moat

OUTLIER OUTLIER POWERHOUSES POWERHOUSES

MATTHIASGIRAUD

SHAWNEEDELANEY

DAVIDBRIER