Boldstart V and Opportunity II, $230mm to back enterprise founders from day one to scale

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L to R, T to B, Ed Sim, Max Heald, Jennifer Moy, Charlotte Chapanoff, Eliot Durbin, Shomik Ghosh, Ellen Chisa, Natalie Ledbetter

I fear not the man [or woman] who has practiced 10,000 kicks, but I do fear the man [or woman] who has practiced one kick 10,000 times. -Bruce Lee

At boldstart, everything we do — how we think, how we operate, how we hustle — is built around helping technical founders with an idea become CEOs of the world’s best enterprise companies. This is our one kick and after 10,000 repetitions a decade later, we are only getting better at leading pre-product rounds and helping mission driven founders go from idea to category creation.

Through specialization of stage (day one, first check) and sector (developer first/SaaS) for 11 years as a firm and 75+ years collectively from our team, it has become second nature for all of us when collaborating with founders on 🔑 early decisions at the beginning of their journey. This includes when and how to monetize an open source project, how to be patient and invest for the long term versus going enterprise too early, when to hire the first account reps, whether to charge for the first POC and how to think about longer term pricing to build a true land and expand model, and… you get the picture. While the answers to these questions are seemingly straightforward, there are nuances that can only be captured and understood by only working with pre-product enterprise teams all day, everyday. Our kick that we’ve practiced over and over has helped our founders go farther, grow faster, and raise over $1.2 billion of follow on capital in the last two years alone.

We are incredibly proud to have led first rounds in now 🦄 like Snyk, BigID, and Kustomer and continue to support the founders as active board members/observers. We’ve also been there at the very beginning with the founders of Superhuman, Front, and Security Scorecard, all of whom were just like you, founders with an idea trying to make a dent in the universe. While there is no one playbook that has helped these founders create new categories or reinvent existing ones, we do know that they all started with an incredible focus on the user and remained true to their product north ⭐️, had incredible product velocity from the start, focused on culture and building a diverse team from the very beginning, and in the face of uncertainty, made swift decisions with confidence and undid the wrong ones even faster. Despite the early success of our portfolio, we’re still trying to get better.

It takes the right village to raise a startup from day one

Getting from idea to Series A and beyond is a tangled path. There’s no prescription. Founders need a true believer in what they are doing, to help them figure out what’s next and be with them when it’s hard to see the path ahead. They also need a village, the right village, one that is exclusively attuned to their needs on day one balancing the scrappiness required to get their initial users and evangelize their product with a longer term focus on setting the right foundation for the future. So we built a community of builders and doers from some of the fastest growing developer first, open source, and SaaS startups to help them navigate the first 365 days. While this community support has proved invaluable, our founders wanted us to do more, to bring more operating 💪🏼, wisdom, insights, and help.

We listened and brought on operating partners like Natalie Ledbetter as our Head of People with significant experience having helped scale three early-stage startups back-to-back. After growing her prior startup from 27 to 300 in a little over two years, Natalie is helping our founders set up world class hiring organizations focused on finding, closing, and retaining amazing and diverse talent. Hiring velocity matters, and Natalie has already helped boldstart founders bring over a dozen key employees to the portfolio in record time.

We listened and most recently brought on Ellen Chisa as Founder-in-Residence, former co-founder and CEO of portfolio company, Dark, a developer first company, to not only invest but also help founders with product strategy, user personas, go-to-market, developer relations, and more. Ellen is also going to build out our knowledge base to help technical enterprise founders at the very beginning of their journey as they make their first hire, develop their first product messaging, build out their initial go-to-market strategy, launch their company for the first time, and more.

One kick, 10,000 more times

We are incredibly 🙏🏼 for all of the founders, limited partners, co-investors, and advisors who have partnered with us and been true believers in our team. We look forward to practicing our same kick 10,000 more times with the next generation of enterprise founders to go farther and faster.

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Looking Ahead

11 years into our journey and nothing is changing about how we collaborate with founders. The only difference is we will have more flexibility in initial and follow-on check size and will be able to provide more operating leverage from the very beginning.

  1. Exclusively focused on enterprise, infrastructure and SaaS with a bias towards product led growth models
  2. ❤️ to meet potential new founders and socialize ideas months before company formation
  3. Provide social proof rather than wait for it. ✍️ the first check and set the terms when everyone else thinks that it’s too early or too crazy.
  4. Lead or co-lead round 1️⃣, invest at formation and pre-product $250k — $4mm, with the ability to invest up to $15mm in life of company
  5. Strive to be the hardest working and most impactful investor
  6. Over-index on long term relationships and goals (i.e, building companies the right way)
  7. Help bring the right angels from our curated list of enterprise founders/execs from the leading open source, SaaS, + infra companies to stack the odds of success
  8. Join a ‘family’ of fellow enterprise founders who are experiencing similar challenges, 🔑 operational wisdom shared daily
  9. Introduce early adopter users/customers from Fortune 500, many of whom have turned into customer #1
  10. 🏗️ a focused portfolio so we can spend more time helping founders realize their milestones faster. 💯 aligned with founders, only enter at first rounds and do not lead A
  11. Believe great founders can build category creators from anywhere and we’ve led rounds in 🇨🇦 🇮🇱 🏴󠁧󠁢󠁥󠁮󠁧󠁿 🇫🇷 🇮🇪 🇩🇪 🇨🇴
  12. Back our founders again and again and again.

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@boldstartvc day one partner + true believer for enterprise Infrastructure/SaaS founders

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