VCs: 5 ways to get founders to hate you

Yrjö Ojasaar
5 min readApr 13, 2023


Sometimes the old standbys like showing up late to meetings, unprepared and then asking “what if Google does this,” or “how do you compete with Facebook” just aren't enough. If those pesky founders keep bothering you — here is the solution!

One or two of these may be enough, but use three, and I guarantee the founders will not hassle you any more.

Les Grossman — Investor Legend

1. Say “No” without saying anything

As a VC you have to say “No” to founder pitches all the time. Some claim that saying “No” is a service, and you should try to help founders develop even when issuing denials. However, the problem with that approach is that founders may then come back with new projects, or recommend you to their friends, entirely defeating your quest for a 4-hour work week and improving your golf game.

Modern VCs should take their “No” game to the next level with the help of technology. Consider investing in ChatGPT software where you can enter the startups strengths — like great early traction, and then the AI writes a response to the founders— “despite the great early traction you have shown, the market size of [insert target market] and financial projections are just not ambitious enough…” If the startup’s strength is their team, then AI will suggest “despite the impressive team you have built, the early traction has been slow …”

For advanced users: Tell the founders to come back to you when they reach xyz MRR, or when they are raising their next round, or when they have Sequoia as the lead investor (for best results ask for all of the above before you will talk).

SuperUsers: You have read PKD’s Minority Report, invest in pre-cognition AI that can predict which founders may contact you in the future, and send them preemptive “No” emails before they get in touch and waste your time.

2. Enlighten the natives with civilized deal terms

Competition among VCs is fierce, so head for the blue ocean of underserved markets. You may be regarded as a daft ignoramus in London or Paris, but in Chișinău or Tartu you can still be a brilliant thought leader.

On your scouting trips to CEE, add to your bag of shiny beads, toilet paper and Levi jeans for the locals your “standard” 3X liquidation preference, super pro-rata and vast veto clauses. The natives will totally fall for your promises of access to investor network, customer introductions and “added value” so they will sign anything.

For advanced users: Get the founders to commit to being “hackers” and “Lean Startup” builders. Then, cut whatever budget and valuation numbers the founders are asking in half — saying that the suggested valuation would be high even in “Berlin” and that building a startup in Sarajevo for a scrappy team should be possible on tap water, forest grazing and bottle deposit returns.

SuperUsers: Explain that the team need to be “closer to market” and demand the founders relocate all their operations, employees and entities to your hometown right away— this way it’s so much more convenient for you to do meetings and unannounced drop-in visits (maybe leave the last part out — the full logic of this move is too much info and could confuse founders).

3. Always tell founders to cut burn-rate

Times are tough, inflation runs rampant so you have been up all night updating your LPs about adding new associates and increasing your pay (the “inflation adjustment”). You may be tired, but you should still take the time to create a “sky is falling” slide-deck for your portfolio founders.

Send founders an email strongly encouraging the firing of at least half the staff, immediately abolishing remote work, and moving out of the office to work from the local library. Warn founders to not look to you for any help or bail-outs, as your portfolio theory guarantees that no one startup is too big-to-fail. To keep your “optimist” credentials conclude the slides with: “Remember: best companies are started in down markets.”

For advanced users: Tell the founders to give away their product/service “Free” — then they will surely grow faster.

SuperUsers: After the advice above, berrate the founder at the next board meeting for insufficient revenues.

4. Always say you invest in the Team

At all startup events, podcasts and blog posts it is vital to repeat how the most important element in your investment decision is the “Team” — makes you look like a top talent spotter and a humanist. If pressed for a number you can even boast that 50% to 75% of the decision is based on the founder team — how will they check ?! If you have the Nobel laureate as CTO — good for you — but does you team have a Pulitzer winner as CMO to craft your message?

However, you must remember to never share your 23 page Investment Memo with anyone, or they may ask why only 3% of the document discusses the Team.

For advanced users: Do all your meetings over Zoom — saves a ton of time! If the founders insist, you can meet the CEO/CTO at your office for a couple hours. As a VC you are such a keen student of the human condition that a couple hours is enough to take in the founders essence and the full team dynamic.

SuperUsers: If you're not sure how to compare different teams just invest in a sociopathic CEO. Leaders without a conscience make for great CEOs because they are very confident, highly charismatic, extremely gritty, absolutely dedicated to success, perfectionists (especially when it comes to others’ performance), and they can pitch like no other since they aren't limited by facts.

5. Apply your life learnings to everyone and everything

Your insights made you tons of money on real estate deals before the 2008 crash ruined everything and you to get a job as a VC. Just because you don't understand the science or technology involved in the project, this should not limit your ability to coach the founders and teach them to emulate your secrets of success. If the hydrogen plane fails to fly — that's no excuse — neither would Robin Williams in Peter Pan — on film they made him soar!

For advanced users: Every startup challenge can benefit from an anecdote of your learnings from 15 years ago. At coaching sessions, conference calls and board meetings take the time to remind the founders how you used free AOL minutes to hang out in IRC to and find customers and made a bundle sell ringtones to them — that should motivate them to action!

SuperUsers: One way to avoid science and learning — don't invest in cleanTech. If there are one things you know for sure — its that God loves: oil and Texas. Otherwise he would not have killed all those dinosaurs 7000 years ago to create the oil deposits for us to pump and enjoy today. To fight His design and reject the joys of His bounty is just liberal heresy!

Tell the founders to solve some real problems — it's absurdly expensive for you to chill your pool in the summer, and it still takes well over 20 minutes to get a kobe beef burger delivered to your house!