Would you cash out or double down?

cash out your business or double down and grow

Would you cash out or double down?

Andrew Roberts spent two decades turning a bootstrapped family company from Brisbane into one of the most widely used text editors on the web, then faced the hardest call of his career: keep a comfortable, profitable business or push for a bigger exit with venture capital and private equity in the mix.

In this Exit Story episode of Built to Sell Radio with Andrew Roberts, you discover how to:

  • Value an acquisition target by asking what it would cost to buy its organic traffic instead of defaulting to a simple revenue multiple.
  • Value your stock when using it as a currency to buy another company.
  • Manage a dangerous dependency on one giant partner and understand how that concentration quietly drags down your valuation.
  • Use buybacks and dividends to get early friends-and-family shareholders paid out while still reinvesting for growth.
  • Decide whether to keep a dividend-paying “cruise mode” business or accept VC money that forces you to pursue a higher-risk, higher-upside exit.
  • Weigh how much equity to roll into a private equity deal when your spouse, your aging parent on the cap table, and your own future all depend on the decision.

Andrew went on to sell Tiny for 10 times his invested capital. Hear his full Exit Story on Built to Sell Radio and see how his decisions around valuation, customer concentration, and rolling equity might shape the way you think about your own endgame.

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