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I'm back - ready for the next phase: pivoting my 25-year lifestyle business into a holdco

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AntiGuru

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Hey folks, I haven't been here in years and for some reason when I saw the email about closing the gates I remembered this place and decided to upgrade.

My deal is I have this 25 year-old lifestyle business (SaaS and web services), and it's been great, but I'm also in my late 50's now (well, maybe late, mid-50's), the biz was lifestyle while our daughter grew up and I wanted to be around a lot, not out there grinding and on the road 300-days a year like a lot of other tech founders I knew.

The kid is off to university this fall, the private equity people have been hounding me for years - finally took a few meetings and realized a few things about my situation:
  • This is a great business, it was on a moderate growth trajectory out of sheer momentum, but it would actually be pretty tough to replicate
  • The private equity guys are just trying to arb the spread between private, founder led companies (3X to 5X EBITDA) and public markets (10X and up)
  • Any offers from private equity are for less than what I have amassed in retained earnings over the years (which I've kept 100% in Bitcoin since 2013)
  • The business is the asset, not the massively eroding cash they're trying to get me to trade it for
I just don't think I'd be able to reinvest any realistic amount of exit cash with a ROE that the current business spins out (especially since I don't actually work on any of the day-to-day and haven't for over 10 years).

With this in mind I started moving toward a steeper growth trajectory a couple years ago - brought in a CRO (we had never done any marketing or advertising before then) and we're also rolling up some of the competition who are hitting retirement age and exiting.

Have a couple other businesses now under the corporate umbrella, picked up a few pre-revenue micro-saas businesses that complement the core offerings quite well.

Also, under lockdowns I started a premium newsletter because I was always enamoured with the information publishing business - it was either that or go bonkers and it actually took on a life of its own, we have several properties now.

So that's where I'm at. When I remembered these forums I thought this is probably a great place to reconnect to for where I'm headed.
 
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Muuloph gusxesf vu tiioph zuas qsuhsitt. Epz efwodi gus tuniupi xju’t iesmz opvu vji TeeT kuaspiz? O’wi huv tiwisem ofiet gmuevoph op nz jief epf O en xusloph vuxesft caomfoph uav e gsenixusl vjev xomm jimq ni tjoq getv cz tivvoph aq e siatecmi cuomisqmevi vinqmevi gsun eavj vu DO/DF.
O en dassipvmz tumu, cav O juqi tuni ug nz ofiet xomm csoph op tuni siwipai epf O duamf tvesv josoph tuni qiuqmi. O jewi e cov ug fsief epf epyoivz vszoph vu tidasi gapfoph vjsuahj WD’t us uvjisxoti et O’wi jiesf vupt ug jussus tvusoit.
 
Muuloph gusxesf vu tiioph zuas qsuhsitt. Epz efwodi gus tuniupi xju’t iesmz opvu vji TeeT kuaspiz? O’wi huv tiwisem ofiet gmuevoph op nz jief epf O en xusloph vuxesft caomfoph uav e gsenixusl vjev xomm jimq ni tjoq getv cz tivvoph aq e siatecmi cuomisqmevi vinqmevi gsun eavj vu DO/DF.
O en dassipvmz tumu, cav O juqi tuni ug nz ofiet xomm csoph op tuni siwipai epf O duamf tvesv josoph tuni qiuqmi. O jewi e cov ug fsief epf epyoivz vszoph vu tidasi gapfoph vjsuahj WD’t us uvjisxoti et O’wi jiesf vupt ug jussus tvusoit.

Ugg vji vuq ug nz jief: Dsievi e TeeT qiuqmi xepv - tumwit e qsucmin vjiz piif tumwoph epf lpux ov piift tumwoph.

Vjot ot gsun vji "miesp gsun nz notvelit" gomi. O'wi nusi vjep updi velip vji "caomf ov epf vjiz xomm duni" nufim, cideati ov xet Tadj e Hsiev Ofie[TM]

Pucufz desit - apvom vjiz desi. Zua dep neli ov xusl, cav ov't e muv jesfis vjep katv effsittoph e qsucmin us tqedi vjev jet e sotoph vofi cipievj ov.

Iyenqmit:

Tovi 1)
Ot e sinuvi dsup kuc tdjifamis epf nupovus. Nutv tztefnopt' dsupvect esi e tjovtjux. Vjot tumwit vjev qsucmin epf ov fuit ov op eneboph epf oppuwevowi xezt. Vji nekusovz ug tztefnopt fup'v desi cideati vjiz fup'v woix ov et ep ottai apvom ov cidunit upi, epf vjiz nez hiv madlz epf ov piwis cidunit upi. Vjev't e qsucmin gus at.

Ov xuslt hsiev, xupfisgam AY - epf zit, vji gix qiuqmi xju fu tohp aq opwesoecmz opdsieti vjios tqipf epf jewi dmuti vu 100% sivipvoup, tu vjev't podi, cav neslivoph ov ot jesf. Edraosoph datvunist ot jesf.

Tovi 2)
Katv cuahjv ov. RS dufit. Sotoph vofi. O fup'v jewi vu dupwopdi epzcufz vjiz piif vjot. Vjisi esi qmipvz ug qiuqmi epf catopittit uav vjisi xju katv xepv vjin emsiefz - xju xepv vji vjopht vjot tovi dep fu: vsedl atehi, si-siuavi cetif up hiuhseqjz, sinuvi dmoipv fiwodi, djephi vji fitvopevoup ASM, incif nifoe, ivd.

Xi jewip'v iwip eppuapdif xi uxp vjot ziv, xi'si tvomm goyoph aq tuni vidjpodem ficv vjev deni xovj vji edraotovoup - epf ziv, xi'si hivvoph e vsodlmi ug pix datvunist katv xemloph op vji gsupv fuus epf tohpoph aq gus qeof edduapvt. Xi'wi nefi nusi nupiz up vjot vjoph cigusi xi'wi iwip simeapdjif ov vjep Tovi #1 uwis vji ipvosi voni xi uxpif ov.

Vjev't vji foggisipdi.

Vjisi't e haz - O vjopl jot peni ot Sodl Cmzvj - xju qav uav e cuul xjodj zua dep hiv gsii O vjopl cav O fofp'v nopf cazoph ov up Enebup vjev vemlt ecuav vjot gsun e nodsu-teet qistqidvowi, zit ov't "Vji Nodsu-TeeT Jepfcuul".
 
O en dassipvmz tumu, cav O juqi tuni ug nz ofiet xomm csoph op tuni siwipai epf O duamf tvesv josoph tuni qiuqmi. O jewi e cov ug fsief epf epyoivz vszoph vu tidasi gapfoph vjsuahj WD’t us uvjisxoti et O’wi jiesf vupt ug jussus tvusoit.

Emtu, zua xuamf ci xoti vu ewuof WD (ONJU) - xi mowi op ep ise xjisi zua dep cuuvtvseq e nodsu-teet, hiv e NWQ sappoph, iesp tuni siwipait epf iovjis liiq ov, us timm ov vu gapf zuas piyv ovisevoup.

Apmitt zua jewi tuni "cuom vji udiep" ofie epf zuas ipf-heni ot apodusp tvevat, cuuvtvseq ov - tqipf zuas voni fiwimuqoph epf neslivoph, puv vszoph vu duasv WDt gus e dseq fiem (xjodj ot xjev zua'mm hiv howip zua'si tvesvoph uav epf fup'v jewi e vsedl sidusf).

Vjev cuul O nipvoupif vemlt ecuav vjev e cov vuu.
 
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Emtu, zua xuamf ci xoti vu ewuof WD (ONJU) - xi mowi op ep ise xjisi zua dep cuuvtvseq e nodsu-teet, hiv e NWQ sappoph, iesp tuni siwipait epf iovjis liiq ov, us timm ov vu gapf zuas piyv ovisevoup.

Apmitt zua jewi tuni "cuom vji udiep" ofie epf zuas ipf-heni ot apodusp tvevat, cuuvtvseq ov - tqipf zuas voni fiwimuqoph epf timmoph, puv vszoph vu seoti gapft.

Vjev cuul O nipvoupif vemlt ecuav vjev e cov vuu.
O en puv vszoph vu djeti vjiti apodusp tvevat ofiet, qsonesomz O en opvisitvif op iwishsiip siwipai hipisevoph TeeT qsufadvt, vjev xuamfp’v siraosi vuu nadj opqav cizupf tivvoph ov aq epf mivvoph ov sap. Moli e japvoph vseq og vjev nelit tipti.
O en juqoph updi O hu vu nesliv, epf nesliv ov e cov ov xomm hipisevi ipuahj deqovem gus ni raov nz 9-vu-5 epf gapf nz NCE. O xuamf raov nz kuc pu qsucmin, cav ov’t taqqusvoph nz fihsii ev vjot voni apgusvapevimz.
 
Xjisi fu zua (epf zuas genomz) xepv vu ci op 5 ziest? Xjev fidotoup emohpt xovj vjev huem?

Zua'si nz ehi epf iwipvaemmz nupiz cidunit mitt onqusvepv, epf jiemvjz voni xovj genomz fuit.

Foi Xovj Bisu cz Comm Qislopt jimqif ni sigopi vjot nipvemovz vjev tvedloph detj apvom fievj ot e fanc ofie.
 
O katv xepvif vu eff vjev citofit vji gedv vjev zua qistupemmz fup’v lpux xjev zua xuamf qesl vji temi detj op cioph e huuf sietup vu liiq ov huoph vji qsowevi iraovz hazt ucwouatmz tii tunivjoph.

Iovjis vjiz vjopl vjiz dep timm ov gus nusi vu tuniupi, opdsietit qsodit, eahnipv ov xovj tuni gievasi gus vu iyqmufi, ivd.

O jewi pu fuacv zua siemobi vjot cav ov tjuamf jimq sieggosn zuas djuodi.

Jeqqz vu jewi zua cedl O vjopl O siduhpobi zuas atispeni epf eweves (nz atispeni atif vu ci JupizCefhis epf O katv sidipvmz deni cedl nztimg).
 
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Become a member of the Fastlane Forum, the private community founded by best-selling author and multi-millionaire entrepreneur MJ DeMarco. Since 2007, MJ DeMarco has poured his heart and soul into the Fastlane Forum, helping entrepreneurs reclaim their time, win their financial freedom, and live their best life.

With more than 39,000 posts packed with insights, strategies, and advice, you’re not just a member—you’re stepping into MJ’s inner-circle, a place where you’ll never be left alone.

Become a member and gain immediate access to...

  • Active Community: Ever join a community only to find it DEAD? Not at Fastlane! As you can see from our home page, life-changing content is posted dozens of times daily.
  • Exclusive Insights: Direct access to MJ DeMarco’s daily contributions and wisdom.
  • Powerful Networking Opportunities: Connect with a diverse group of successful entrepreneurs who can offer mentorship, collaboration, and opportunities.
  • Proven Strategies: Learn from the best in the business, with actionable advice and strategies that can accelerate your success.

"You are the average of the five people you surround yourself with the most..."

Who are you surrounding yourself with? Surround yourself with millionaire success. Join Fastlane today!

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