『EP 16: Why I'm Worried About My Friends' "Successful" Acquisitions』のカバーアート

EP 16: Why I'm Worried About My Friends' "Successful" Acquisitions

EP 16: Why I'm Worried About My Friends' "Successful" Acquisitions

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 Why undisclosed acquisition prices should worry you. A bootstrap founder's analysis of the "successful" startup exits that may not be so successful - and why starting over in your thirties isn't a winning strategy.The pattern that's making me worried:Two friends' startups acquired in past two months, five in past two yearsAll labeled "successful acquisitions" but zero price disclosuresCompare to OpenAI buying hardware startup for $1 billion - that number got announced immediatelyWhen acquisition prices aren't disclosed, it's usually not good news for foundersThe brutal acquisition math nobody talks about:Company sells for $5 million (sounds decent, right?)VCs get their $3 million back first due to liquidation preferences$2 million left to split among founders and employeesIf you own 50% after dilution, you get $1 millionAfter taxes: $500-600K for 3-4 years of workSenior engineering jobs at Google would have paid moreWhy the free money era ending hurts VC-backed startups:Haven't seen funding announcements on LinkedIn in 2-3 years2020-2021: constant $6-15 million seed round announcementsCompanies that raised at 10-50x revenue multiples can't raise follow-on roundsForced into "rescue acquisitions" for whatever they can getThe pivot problem with investor boards:Recently pivoted SimpleDirect quickly (new website at getsimpledirect.com)With VCs on board, this speed would be impossibleSignificant pushbacks, potential lawsuit threatsFriends with investors couldn't pivot fast enough when neededBasecamp vs Asana - the ultimate comparison:Basecamp: Founded 1999, 60 employees, $280 million revenue in 2024Asana: 1,819 employees, $3 billion market cap (down 32% this year)Basecamp founders control and split most of that $280 millionAsana founders own tiny percentages of potentially failing public companyThe energy cost of restarting in your thirties:5 years building + 6-12 months fundraising + 3-6 months acquisition talksWalking away with less than hoped, having to start over at 30+Recently felt this dread myself when considering SimpleDirect changesThe compound advantage of never having to restart vs. exit-restart cycleThe new playbook for 2025-2026:Build for actual profitability from day one - not "path to profitability"Keep teams small and efficient - companies getting acquired scaled headcount faster than revenueBuild for control, not growth - better to own 100% of $5M company than 20% of $25M companyThink in decades - have real moats and roadmaps, not quarterly thinkingWhy bootstrap founders have the advantage:Don't have to play the macroeconomics game you can't controlCan focus 100% on product, customers, and profitability4-5 years runway because we don't burn massive cash like 1,800-employee teamsEvery month builds on previous month's foundation - compound growth vs. restart cyclesThe chess piece reality:Taking VC makes you a piece on their board, not the playerYou move according to market forces and investor demandsDoorDash co-founder owns 0.23% after multiple funding roundsPublic company scrutiny adds compliance, lawsuits, more complicationsQuestions every founder should ask:Can I do this with a smaller team?Am I building for exits or thinking in decades?What happens if I can't raise another round?Do I actually need outside capital right now?Red flags you're heading for a disappointing exit: Raised in 2020-2021 bubble, can't raise follow-on rounds, scaling expenses faster than revenue, limited pivot flexibility due to investor constraints.Bottom line: The bootstrap mentality of "we don't exit, we compound" is being validated. While talented founders restart their careers at 30 after disappointing acquisitions, bootstrap founders build on existing foundations monthly. There has to be a better way than working essentially for free for years.New episodes Monday/Wednesday/Friday at 9am EST. Real founder lessons, not startup theater.Daily thoughts: @TheGeorgePu on Twitter/XFull episodes: founderreality.comEmail: george@founderreality.com
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