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Both Sides of the Table

2 resources from Both Sides of the Table we point founders to, and the questions each answers.

📄 Article
Free Intermediate

Why we picked it Suster, a former founder turned VC, hands you the exact line for the advise-versus-decide boundary: when he disagrees with a CEO he says, 'I see it slightly differently, but you live in this business every day so I'll yield to your judgment. Let's revisit in 6 months.' That is the move in reverse: you can steelman your investor's push, name your disagreement out loud, then take the wheel and set a checkpoint, so no one feels steamrolled and the relationship survives the 'no.'

8 Tips To Get the Most Out of Your Investors and Board

From Both Sides of the Table by Mark Suster 12 min read

  • Board members advise, the CEO decides. Debate hard, then go make the call with your exec team, don't let the board meeting become an approval meeting
  • Formalize a disagreement with a revisit date ('let's check in 6 months') so a 'no' reads as conviction plus accountability, not stubbornness
  • Earn the right to push back forcefully by over-communicating and building a real relationship with each investor long before the hard conversation
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Answers One of my investors is pushing hard for a strategy I disagree with. How do I say no without burning the relationship?
✍️ Essay
Free Beginner

Why we picked it This is the original essay that coined "lines, not dots," the exact idea behind the opinionated answer. Suster (a VC who himself took 15+ meetings with a founder over two years before investing) argues that on a single meeting you are a dot with no track record, so a cold pitch during your raise is the weakest possible position. He tells founders point-blank to meet investors 6 months early, say you are not raising yet, and tell them what you will have achieved by the next meeting, so the investor watches you become a line.

Invest in Lines, Not Dots

From Both Sides of the Table by Mark Suster 9 min read

  • One meeting makes you a dot; investors gain conviction from a line of meetings that show you hitting what you said you would
  • Meet target investors months before you raise, explicitly say you are not raising yet, and state what you will have done by next time
  • If someone invests in you as a dot (fast, no diligence, max price), they are a dot to you too, and you barely know who now owns your cap table
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Answers How do I build a relationship with an investor months before I actually need to raise?
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