November 17, 2022 Company Building

Costanoa’s First 10 Years: What a Long (and Short) Strange Trip It’s Been

The Costanoa team at our 10-Year Celebration.

I’ve gotta say, the last ten years have been more than I bargained for. More difficult and more bumps, for sure. But also more fun, more inspiring and more energizing than I ever could have anticipated. I guess that’s true for just about every founder. What an amazing journey the last ten years have been! I thought I’d take a minute to look back over the last decade, before we turn our attention to the next one. Here are a few things I’ve learned:

  1. Founders are awe-inspiring. They jump off a cliff with nothing more than an idea and a dream. They think “maybe I can recruit some people, solve a customer’s problem, raise some capital … and maybe it will work.” It’s worth stepping back to see how crazy that is by conventional standards – and how absolutely incredible it is that it works as often as it does. 
  1. My most important job: picking people I want to work with. For a long time. Yes, I look for people with deep knowledge/empathy/curiosity for their customers/problem, people with incredible drive, tenacity and resilience, people who can recruit the first best talent in the world’s worst hiring environment. But I also look for people I’ll enjoy working with. Many VC’s – and founders – don’t select for this. I didn’t always either, earlier in my venture career. But, for me now, life’s too short. We’re going on this journey together, figuring out the business as we go and bringing others (employees, execs, other investors) into the business, which is often built around the strengths (and weaknesses) of the founders. To do that, we have to have trust and good, direct communication. We’re going to log some hours in tough situations and have some difficult conversations. I’m happy to do it – win, lose or draw – as long as I’m working with quality people. And there are more than enough great founders who are also great humans I want to work with that I don’t need to do anything else.   
  1. I’m the hen. To quote Jim Barksdale, “when it comes to breakfast, the hen is interested. The pig is committed.”  As much as I care and am deeply invested in the success of each company I invest in, no one owns it like a founder. 
  1. Starting Costanoa made me more empathetic to founders. I now know what it’s like to have it all on the line and be ghosted by investors, something I’m embarrassed to say I didn’t really understand before. So I’m now much quicker to decline a meeting than I used to be. While it’s not what founders want to hear, for sure a quick no is better than a long and tortured one. And I hereby apologize to past founders where I worked too hard trying to force fit something that wasn’t going to work. You’d have been better off if I’d said no faster.
  1. Be direct even when it’s hard. I’ve become more responsive, respectful and clear in my communications. Before Costanoa, I wasted too much time and energy trying to be diplomatic, especially in difficult conversations. I’ve learned that the best way to care for others is to share what I’m thinking directly and help drive the business forward. 
  1. Growth mindset > the grind. In the early days of Costanoa,. I was grinding to raise Fund I, worried about failing, couldn’t figure out how to catalyze the first close – and then my daughter tore her ACL. I spent a weekend unable to get out of bed, afraid. I eventually pushed through, but knew I needed better tools. Carol Dweck’s Growth Mindset was it for me, thanks to Amy Pressman, founder &CEO of Medallia. I used to think I knew a lot, and could grind through anything. I don’t anymore. Instead, I try to keep learning, keep asking questions, keep getting better – and got comfortable living with a lot more ambiguity. And understanding better the many facets of humility. Humility to understand the limits of my knowledge, even when I’ve done the work. Humility to recognize that founders have lots of choices – and that it’s an incredible act of trust to partner on your best idea and most valuable asset with an investor and board member who you can’t fire. Humility to remember in a boardroom that, while I might have spent six hours on the company this month, the management team has spent 60-70 hours this week. And humility to understand that LPs have so many investment options in and beyond venture. The idea that they’re willing to give millions of dollars to a brand new venture firm in a blind pool for at least a decade is practically a miracle.
  1. Winners are where you make your money; failures (and hard times) are where you earn your reputation. Enough said.
  1. The world is both bigger and smaller than it used to be. The start-up ecosystem that was once Silicon Valley is now the world. I used to hear, “I won’t invest in any company I can’t drive to” and “I won’t invest unless the whole team works together in one place.” That’s incomprehensible in today’s ecosystem. Great companies come in all kinds of places and configurations. And we’re all better for it. 
  1. Start with your core values. Organizations can only manage so many priorities, and leaders have to make setting the culture a priority or it won’t happen. For me, DEI has always been important. But when I started Costanoa in 2012, I was just trying to get the firm launched and survive. So Costanoa looked like most VC firms – very white and male  I’m not proud of that fact, but it’s true. It took a few years before we made DEI a priority as a firm and across our portfolio. Costanoa is now 60% female and 40% PoC, and we continue to work with all our companies to make their workplaces more diverse and inclusive. It’s a journey, not a destination, and we’re on the path. But we’d be in a different and better place if we’d started earlier.
  1. Building an organization is the most incredible fun.  Setting and shaping culture, bringing in extraordinary people and giving them room to grow and run (which, in turn, creates an environment that is shaped by the team) is like watching a kid grow up and become an extraordinary adult. Now, as a founder myself, I’m much more intentional about the environment and kind of people I surround myself with. I’m just as driven to win as ever, but now I’m trying to do it by being a positive force. By treating every person with respect. And by creating an environment where extraordinary people can take on hard projects, be transformed by the experience, and accomplish things they didn’t know they were capable of.

I’ll end with this. Those of us in early stage VC get to do something that seems completely crazy by most of the world’s standards. We bet on people before they have companies, and companies before they have product. We pick founders who haven’t done it before because we see their promise and drive. And yet: somehow it all works. It is a world of wonder, like staring up at the stars. Let’s never forget that.



Written by


Founder & Managing Partner

Greg Sands