What 100% of startup founders say about their investors


More than 200 founders later

In 2024, I've spent time with more than 200 different startup founders. I've worked deeply with several as coaching clients or helped them tell data stories to accelerate their businesses. I've gotten to know many more in introductory conversations, at events, and in their search for customers and investors. These conversations have informed a lot of the writing I've done about startups this year, especially in AI (where it is hard to build effectively, hard to sell, and hard to raise later-stage rounds).

Founding is a difficult and lonely road, and much of what founders have shared resonates with me. When Mallun Yen pitched me on joining Operator Collective as their first Founder in Residence, specifically to better support founders both in and outside the portfolio, I saw an opportunity to better systematize and scale the work I've been doing with founders this year.

As you may have seen, I said yes!

What founders wish they had

I had a good idea of the kinds of support that would help founders from all these conversations and from my own lived experience. However, before I built anything significant, I wanted to collect founder POV more rigorously. Over the last 6 weeks, I've collected perspective from 100 founders that I hadn't worked with previously. Their feedback is remarkably consistent and matches what I felt as a founder myself.

Above all else, founders want their investors to provide high-quality connections to potential customers. All 100 founders that I spoke with mentioned this. At Textio, I had one investor who did this very consistently. (Spoiler alert: It was Mallun, with whom I'm now working at Operator Collective.)

Founders have consensus around some other items too. They want access to good benchmark data for comp and metrics, connections to domain experts and coaches, and great fractional support. They said things like:

  • “Help me find 3-5 early customers who can give us real feedback - with so many startups trying to do the same thing, the real differentiator is having feedback and really building a genuinely good V1 product vs. shipping a half baked solution.”
  • “It is beyond demoralizing when you don’t use my product. Please become a customer yourself when you invest! That’s the thing that makes you credible to introduce me to other potential customers, which we need help with.”
  • “The best thing my investor ever did was connect us to their old CFO who worked 10 hours a week for us heading into our last round.”
  • “Can they get my exec team support from people who have actually done it, recently?”
  • “Get me access to a coach who won’t immediately tell my investor about all the problems I’m having.”
  • “She [VC] is literally in the green room with Taylor Swift and her people. I make a creator platform. Why did I not end up with an intro to Taylor’s marketing people?”

Founders are also clear on the so-called help that isn't actually helpful. Top of the list: shoot-from-the-hip product and marketing ideas, followed by being told who to hire and fire.

One founder sums it up pretty well: “The worst is when someone thinks they’ve offered the solution to a hard problem, without doing the work to think it all the way through.”

Data is only as good as the action you take

It seems like every venture firm these days is offering their version of The Authoritative Incubator or Accelerator, mostly geared towards helping companies raise new rounds of venture funding. This can be quite valuable! However, it's clear from the data that founders want less support pitching their companies and more support actually achieving the customer milestones that allow them to keep growing in the first place.

Based on this input, I'm prioritizing three things as Founder in Residence:

  • Giving founders real, practical opportunities to get in front of potential customers
  • Tapping into Operator Collective's incredible community of senior operators to advise founders and offer fractional support to help them accelerate faster
  • Offer coaching and support not just for CEOs, who get most of the resources today, but for other founders and early team members too

And, thanks to the incredible partnership of Anna Jacobson (who, as Operator Collective's Operations and Data Partner, has built one of the most impressive data infrastructures I've ever seen in this industry!), we're going to systematically measure how well these programs work for founders, and adjust as we go. I see more data stories in the future!

If this sounds like something you'd like to be involved with, either as a founder or an operator, I'd love to hear from you. And if you'd like to follow along with this work at Operator Collective, you can sign up here.

Thanks for reading!

Kieran


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