Video of My Appearance with Jason Lemkin on SaaStr Workshop Wednesdays

Last Wednesday I had the pleasure of sitting down for a 50-minute chat with SaaStr founder Jason Lemkin as part of their Workshop Wednesdays program.

Our ostensible topic was What Really Matters in SaaS in 2025, but we ended up having a wide ranging and fast-paced conversation about many things, including:

  • Will 2025 be the year of IPOs for PE-backed companies?
  • What metrics are PE sponsors looking for in mid-market software acquisitions?
  • What’s happened historically to the IPO bar, i.e., the minimum size you need to go public, and where is it today?
  • Are PE firms looking for fixer-uppers or already-fixed businesses?
  • Jason’s rule of 20/30/0 = to get PE interest, you need $20M in ARR, 30%+ growth, and 0% cash flow
  • How to get a strategic multiple from a PE firm?
  • A discussion of Andy Wilson‘s successful exit at Logickull where Jason was an investor and I was an advisor.
  • What will be the impact of AI on SaaS budgets? (Here, we discuss some data from the Battery report on State of Enterprise Technology Spending.)
  • How to target and win “experimental AI budget” (that is out there and in no short supply)?
  • How some customer success orgs lost the plot, and became too focused on process (e.g., QBRs) and not enough on sales and renewals.
  • My rule of 30: that expansion ARR should be 30% of new ARR, roughly. Too high and you’re milking the base, and too low and you’re ignoring it
  • Why I love the healthy tension between sales and customer success when they are separated
  • What a “slug” or “zombie” company should do if you’re $15M and growing at 15%
  • Should companies lead or follow on pricing models? (We both firmly believe in using the same pricing model as the leaders in your sector unless you are a pricing model disruptor.)

Here’s the video. Thanks to Jason for a great conversation.

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