Announcing Boldstart IV and Opportunity I, $157mm to back enterprise founders from day one to scale

Ed Sim
Ed Sim
Nov 12 · 4 min read
Team boldstart: Front Row L-R: Sparky, Ed Sim, Eliot Durbin, Back Row L-R: Jeff Leventhal, Charlotte Chapanoff, Max Heald

“It’s a dangerous business, Frodo, going out of your door,” he used to say. ‘You step into the Road, and if you don’t keep your feet, there is no telling where you might be swept off to.’

Frodo quoting Bilbo Baggins in The Fellowship of the Ring, J.R.R. Tolkien

Bilbo’s words also speak of the founder’s ‘Road’. Taking that first step and starting a company leads one on an exciting, exhilarating, and often difficult journey. Earning the right to join founders at the very beginning inspires us every day. Helping them ‘keep their feet’ is why we created boldstart.

In a time of mega funds and the continued productization of venture capital, we believe founders, more than ever, need a day one partner who is experienced, patient, and wise, one who practices the art as much as the science of startups; and one who enjoys the journey and not just the destination. Founders need true believers who are as passionate and bold as they are when building what others may think impossible. They need partners who support and challenge them to become a better CEO and leader. They need guides who will help them create enduring companies and understand that, for some, focusing on developer and customer love before revenue may be more important than anything else.

In almost a decade (twenty years for some of us) of being a first check partner for enterprise founders, we’ve learned there is no one path that founders can take to achieve product market fit. We’ve learned the key to being a great partner is to actively listen. It’s having the perspective to tailor advice for each specific founder and company. It’s having the experience, relationships, and network of go-to-market builders and Fortune 500 CIOs to enable founders to do things smarter and faster. Ultimately, we are here to provide entrepreneurs with options and leverage to accelerate their current path, or to choose a new one.

In the past six months, a number of our companies have scaled and raised over $250 million of follow-on financing from leading investors like Accel, Andreessen Horowitz, Battery, Bessemer, Lightspeed, Redpoint, Sequoia, and Tiger Global. There is no better feeling than watching founders go from “day one” to market leader with us by their side. We’ve helped founders ‘step into the Road’ and invent new enterprise categories like developer security (Snyk), data privacy (BigID), professional paid email (Superhuman), security ratings (Security Scorecard), customer first support (Kustomer), and process discovery (FortressIQ). And we have still more entrepreneurs whose startups are on the cusp of making their mark.

The Adventures Continues, Boldstart IV and Opportunity Fund I

Like our founders, we went out the door with a vision and small initial round/fund of $1 million. Nine years later, we are 🔥 up to announce two oversubscribed funds; Boldstart IV, $112mm to lead first rounds, and Boldstart Opportunity I, $45mm to continue backing the best companies in our portfolio at Series C and beyond.

We are grateful for the founders who believed in us as their first partner, our Limited Partners who have been true believers in us through multiple funds, our newer institutional LPs who have joined the family, and our CxO and GTM advisors as they’ve been a huge help giving founders product feedback, becoming first customers, and providing expert operational advice. We’d also like to thank the many co-investors who have provided us and our portfolio with meaningful support. It takes a village to build an enduring enterprise company, and we are grateful to have all of you in our family.

Looking Ahead

Nothing is changing about how we work with founders. The only difference is we will have more flexibility in initial and follow-on check size.

  1. Exclusively focused on enterprise, infrastructure and SaaS with a bias towards product led growth models
  2. Over-index on long term relationships and goals (i.e, building companies the right way)
  3. ❤️ to meet potential new founders and socialize ideas months before company formation
  4. 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.
  5. Lead or co-lead round 1️⃣, invest at formation and pre-product $250k — $2mm, with the ability to invest up to $10mm in life of company
  6. Help craft initial cap table with network of enterprise founders and executives to stack the odds of success
  7. Backed by a ‘family’ of fellow enterprise founders who are experiencing similar challenges, 🔑 operational wisdom shared daily
  8. Introduce Fortune 500 CIOs/CTOs during diligence process for feedback
  9. Strive to be the hardest working and most impactful investor
  10. 🏗️ a focused portfolio so we can spend more time helping founders realize their milestones faster
  11. 💯 aligned with founders, only enter at first rounds and do not lead A
  12. Back our founders again and again and again.

We’ve been investing out of Fund IV for the last 12 months. Our portfolio reflects the idea that great companies can be built anywhere. With NYC’s wealth of Fortune 500 customers and the rapidly evolving enterprise startup market, we are a key bridge between the west coast, Europe, Israel, and Canada.

Current Fund IV portfolio stats (all companies in stealth):

  1. Stage at Investment (mostly day one) — 3 company formation, 4 slide deck only, 1 alpha product
  2. Geography — 1 NYC, 2 Bay Area, 2 Canada, 1 Portland, 1 London, 1 Israel
  3. Teams — 6 partially distributed, 2 fully distributed
  4. Early Model — 5 developer first, 3 top down enterprise sales
  5. Infrastructure 7/Saas 1
  6. Experience — 5 first time founders, 3 repeat founders

If you’re like Frodo and Sam taking your first steps out of the Shire on the enterprise ‘Road’ and seek a day one partner, please DM us @boldstartvc

boldstart ventures

Ed Sim

Written by

Ed Sim

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

boldstart ventures

first check lead for technical enterprise founders

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