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boldstart 2023 recap

  • 12.22.2023

2023 was a year of extremes. The world experienced both the lowest of lows and the highest of highs. It was a stark reminder that gravity is a powerful force, and that the world is not built to continually grow and increase in value 📈. Geopolitically, the Ukraine War raged on with no end in sight, and we all experienced a new crisis with the terrorist attacks on Israel by Hamas. The startup climate was less than stellar as we were impacted by rising interest rates, a 22-year high inflation number, and a massive slowdown in venture capital investments. However, the Nasdaq rose over 40%, and we underwent the beginnings of one of the greatest platform shifts in history with the rise of AI technology being infused seamlessly into every single application. We are also at the tail end of a two-year journey to streamline costs, become more efficient, and financially fit to prepare for balanced growth in 2024.

Against this backdrop, we believe our statement from our 2022 recap rings truer than ever; this cycle will be the best time to deploy capital as only the best and 😜 founders on a mission will start companies now, building lean and mean from day one. To that end, we’re super 🔥 up as we partnered with 8 new founding teams this year who are all still in stealth. In addition, enterprise software budgets are poised to continue to grow double digits, and founding teams are hyper-focused building lean and efficient from the start which lead to some amazing companies being built in the class of 2023 and 2024.

We’re also super excited to kick off 2024 not only because of future interest rate cuts, but also because it’s the year of the dragon 🐲 or year of the fund maker in VC terms!

Thanks again 🙏🏼 to our founders, limited partners, co-investors, and friends for your continued partnership, support, and encouragement.

With that, here’s a recap of our year.

Inception Investing

We coined a new term “Inception Investing” to help founders who are just getting started and thinking about starting company to have one place to go to raise that round.

Here’s why. Pre-seed isn’t first anymore since according to Pitchbook, the median age of startups who raise a pre-seed round is now 1.2 years. In addition, pre-seed rounds tend to be quite small in the less than $2M range. Seed is also not first as the median age is now 2.7 years. We also have everyone under the sun racing to be first on the cap table from angels to pre-seed investors to seed VCs to multistage funds where round sizes now range from $500k — $10M!

Enter the new era of “Inception Investing” to describe our approach.

Inception Investing means engaging with founders well before they incorporate, helping them battle test and iterate their ideas, helping them pre-sell some of the initial hires, and leading those rounds upon company formation so founders can run fast out of gates and not spend months trying to raise capital.

This is not incubating, since that’s not scalable unless that is all you do. This is pre-accelerator since, well, you have to be incorporated to join, and this is pre-Pre-Seed. This is also what boldstart was built to do from our founding in 2010; it’s just a new name.

Ed had the opportunity to talk about this approach on Harry Stebbings’ Podcast, 20VC, and it clearly hit a nerve as it reached over 1 million plays in the first 24 hours. We also wrote more about it on our blog here.

Portfolio company activity

We also had an active year partnering with new founders as well as experiencing new milestones with existing portfolio companies — here are some stats from the past year:


Last year, Ed wrote about his move to Miami. We’re now in Year 2 as a distributed team covering San Francisco, Boston, and Miami with frequent trips to NYC. This past year, we expanded and are now global! Our new Operating Partner, Anna Debenham, joined us from London by way of Snyk where she was Employee #4 through scale. We can now work even more closely with our founders across 8 time zones.

boldstart also received some recognition this year as Ed Sim was selected as the #1 Seed Investor on the Insider Seed 100 as well as to the Midas Seed List (#9) for the second year in a row. Ellen Chisa was selected as one the 52 Most Important VCs in Boston for the second year in a row. This is a testament to the work of the entire team and more importantly our founders.

The team also had an active year publishing content that’s useful for our founders (and future founders). We also have a Partner with a podcast! Shoutout to Shomik Ghosh who finally launched a podcast for the boldstart team with his Software Snack Bites — it’s a must listen!

Here are some of those resources:

  • What’s Hot 🔥 in Enterprise IT/VC A weekly newsletter written by Founder and General Partner Ed Sim, containing his musings, notes and readings around the latest in enterprise VC, software, and scaling startups.
  • Software Snack Bites Curated by boldstart Partner Shomik Ghosh, Software Snack Bites is your go-to spot to learn about enterprise software, trends, and concepts that we’re seeing in the software ecosystem.
  • Dev First Founder Toolkit A collection of blog posts, templates and resources which we’ve created specifically for Dev First founders of startups.
  • Ellen’s Newsletter The newsletter of boldstart Partner, Ellen Chisa, with material related to early stage startups, particularly product, developer relations, and VC.
  • Cryptosis A newsletter all about Crypto, curated by boldstart Associate Ernest Addison.


Charlotte was promoted this past year to Head of Marketing and Global Events and quckly we ramped up our event cadence. One of the highlights from this past year was our week-long takeover of a hotel around RSA Security in San Francisco. We kicked it off with a CISO panel on Sunday night and found that the most valuable time was spent in the off hours where over a dozen founding teams in cybersecurity were able to share notes on customers, partners and investors. We look forward to doing this again in 2024!

Besides RSA, we also continued hosting curated dinners across the globe, running the Miami Enterprise Infrastructure Meetup, and in November hosting our AGM investor meeting in Miami 🌴.

It’s great to see so many events are back in the calendar after such a long hiatus. And yes, those steak 🥩 dinnahs do help close deals!

If you’re a technical founder about to start a company and want a partner from Inception, DM boldstart or any one of us:

Here’s to the year of the Dragon 🐲!