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 years
• All labeled "successful acquisitions" but zero price disclosures
• Compare to OpenAI buying hardware startup for $1 billion - that number got announced immediately
• When acquisition prices aren't disclosed, it's usually not good news for founders

The 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 employees
• If you own 50% after dilution, you get $1 million
• After taxes: $500-600K for 3-4 years of work
• Senior engineering jobs at Google would have paid more

Why the free money era ending hurts VC-backed startups:

• Haven't seen funding announcements on LinkedIn in 2-3 years
• 2020-2021: constant $6-15 million seed round announcements
• Companies that raised at 10-50x revenue multiples can't raise follow-on rounds
• Forced into "rescue acquisitions" for whatever they can get

The pivot problem with investor boards:

• Recently pivoted SimpleDirect quickly (new website at getsimpledirect.com)
• With VCs on board, this speed would be impossible
• Significant pushbacks, potential lawsuit threats
• Friends with investors couldn't pivot fast enough when needed

Basecamp vs Asana - the ultimate comparison:

• Basecamp: Founded 1999, 60 employees, $280 million revenue in 2024
• Asana: 1,819 employees, $3 billion market cap (down 32% this year)
• Basecamp founders control and split most of that $280 million
• Asana founders own tiny percentages of potentially failing public company

The energy cost of restarting in your thirties:

• 5 years building + 6-12 months fundraising + 3-6 months acquisition talks
• Walking away with less than hoped, having to start over at 30+
• Recently felt this dread myself when considering SimpleDirect changes
• The compound advantage of never having to restart vs. exit-restart cycle

The new playbook for 2025-2026:

1. Build for actual profitability from day one - not "path to profitability"
2. Keep teams small and efficient - companies getting acquired scaled headcount faster than revenue
3. Build for control, not growth - better to own 100% of $5M company than 20% of $25M company
4. Think in decades - have real moats and roadmaps, not quarterly thinking

Why bootstrap founders have the advantage:

• Don't have to play the macroeconomics game you can't control
• Can focus 100% on product, customers, and profitability
• 4-5 years runway because we don't burn massive cash like 1,800-employee teams
• Every month builds on previous month's foundation - compound growth vs. restart cycles

The chess piece reality:

• Taking VC makes you a piece on their board, not the player
• You move according to market forces and investor demands
• DoorDash co-founder owns 0.23% after multiple funding rounds
• Public company scrutiny adds compliance, lawsuits, more complications

Questions 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.

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