Ed Sim is the Founder of boldstart ventures, a true believer and partner from inception for bold founders reinventing the enterprise stack. Ed is currently on the boards of Snyk, BigID, Blockdaemon, Protect AI, Env0, and several other cybersecurity and infrastructure startups. Other notable inception investments include Kustomer, where he was on the board until his exit to Meta, Superhuman, Security Scorecard, and Front. Ed also co-founded MState in 2017, an enterprise blockchain lab in partnership with IBM, where seed investments include Fireblocks. He is known for being a partner from inception, helping founders start, scale, and exit while enjoying the process.
Ed has been recognized as a top 10 investor on the Forbes Midas Seed List for the last three years and as the No.1 seed investor in the Business Insider Seed 100 for 2023 and 2024. He also writes the popular weekly newsletter What’s Hot in Enterprise IT/VC, which covers the latest trends in venture capital and enterprise technology. Prior to boldstart, Ed was a Co-founder of Dawntreader Ventures, where he led inception investments in Greenplum (sold to EMC, Pivotal — IPO), GoToMeeting (sold to Citrix), and LivePerson (IPO). He graduated from Harvard with a BA in Economics and was a four-year letterman on the men’s lacrosse team.
Here’s a glimpse of what you’ll learn:
- [0:41] How Ed Sim’s career blossomed over 25 years in the venture world
- [2:40] What does it take to be a successful entrepreneur and investor?
- [4:09] New York’s evolution as a tech powerhouse and what it means for enterprise software
- [7:13] How pre-seed and seed rounds came to be, and why we need Inception rounds
- [11:33] How Ed’s lacrosse background shaped his investment philosophy
- [18:33] The importance of finding a balance between “steak” and “sizzle” in founders
- [22:03] AI’s future and how incumbent companies may compete or collaborate with startups
- [25:49] An insider’s advice on evaluating companies with “intuitive TAM”
- [40:34] The key to sustained content creation discipline and its importance in venture capital
- [54:28] Ed’s long-term vision for boldstart ventures
In this episode…
What does crafting overnight success stories in the complex tech landscape take? Passion, resilience, and a sharp eye for pioneering technology can ignite the path to building billion-dollar enterprises. Can these same elements apply regardless of market conditions and trends?
Seasoned venture capitalist Ed Sim lays out his blueprint for venture capital triumph, infused with lessons learned from his early days selling kitchenware to standing at the helm of a game-changing tech investment firm. He highlights that the path to industry leadership is paved with a long-term vision, founder empathy, and a focus on problem-solving. With insights on how significant shifts reshaped the stage — such as the adoption of Amazon EC2 and open-source — Ed demonstrates a keen ability to anticipate and leverage the market’s evolutionary trends. He offers invaluable guidance to aspiring venture capitalists and seasoned investors alike, proving that relentless commitment and strategic evolution withstand the test of time.
In this episode of Driving Alpha, Steve Brotman chats with Ed Sim, the Founder of boldstart ventures, about Ed’s growth in venture capital and insights into modern tech investments. Ed shares the strategic thinking propelling his journey, emphasizing early participation in startups and an unwavering dedication to enterprise infrastructure. He also elaborates on the critical role his passion for sports and grit played in forging relationships and sustaining success through economic cycles.
Resources mentioned in this episode
- Steve Brotman on LinkedIn
- Alpha Partners
- Ron Insana: LinkedIn | Website
- Ed Sim: LinkedIn | X | Newsletter – What’s Hot in Enterprise IT/VC
- boldstart ventures
Quotable Moments:
- “Alpha Partners works with over 1,100 VCs looking to partner with them on their best later-stage opportunities.”
- “I love working with engineering-driven founders with bold ideas and laser-sharp focus on product well before writing their first lines of code.”
- “It’s amazing by the way. I remember we kind of had that Rodney Dangerfield-like feeling — we get no respect.”
- “If I have an idea, I might not even have shipped any software yet, but I need capital. Who do I go to?”
- “We wanted to specialize in enterprise software. And people were like, ‘You’re freaking nuts’.”
Venture Tips from Ed Sim:
- Pursue your passion in venture capital: Investing in what genuinely excites you fosters long-term dedication and success.
- Stay ahead by focusing on second-order effects: Look beyond obvious market trends to identify emerging opportunities as technology progresses.
- Embrace user empathy and strategic storytelling: Balancing users’ immediate needs with a compelling long-term vision is key to attracting investment and support.
- Maintain content discipline to cultivate relationships: A consistent content strategy, such as a newsletter, can enhance your reputation and establish trust with founders and investors.
- Embed steadfastness in your business philosophy: Expect hardships in establishing a VC firm — prepare with grit, strong partnerships, and resilience for a thriving venture career.
Episode Host: Alpha Partners
This episode is brought to you by Alpha Partners, an NYC-based growth equity firm managing $300 million.
Alpha co-invests in top-tier growth equity companies led by the world’s best investors. We focus on scaling and late-stage tech investment opportunities primarily in the essential technology sector, including e-commerce, enterprise software, fintech, edtech, and health IT.
To learn how we can help you with your funding goals, visit www.alphapartners.com, or email us at vc@alphapartners.com.
Sponsor Host: Affinity
Affinity is a relationship intelligence platform that empowers dealmakers in relationship-driven industries to find, manage, and close more deals. With the most automated relationship intelligence insights and technology, Affinity enables leaders to drive deals and ensure their teams can take action with confidence, knowing the context and history of every relationship.
The Affinity platform, including Affinity CRM, is used by over 3,000 relationship-driven organizations worldwide. Founded in 2014, Affinity is headquartered in San Francisco and backed by leading investors, including Menlo Ventures, Advance Venture Partners, 8VC, and MassMutual Ventures.
Learn more at affinity.co/drivingalpha.
Episode Transcript
Intro 0:06
Welcome to Driving Alpha, where we feature our friends, the outperforming investors, who demonstrate their past to driving alpha or outsized investment returns. We’re Alpha Partners, where we partner with 1000 early-stage venture firms as their opportunity capital to invest in their best companies.
Driving Alpha is supported by affinity, provider of the CRM for the private capital relationship economy. Affinity knows who has the best relationship with the right startup. Affinity knows. Learn more at affinity.co\drivingalpha.
Steve Brotman 0:41
Hi, I’m Steve Brotman. I’m the managing partner at Alpha Partners, and this is Driving Alpha. Our podcast focused on, primarily on investors and VCs in particular, that we think drive alpha. Alpha Partners works with over 1,100 VCs looking to partner with them on their best later-stage opportunities. We’ve been doing this for about a decade, and in my own career, I’ve been working in venture for about 25 years, and one of the gentlemen that we’re interviewing today is Ed Sim. He’s of the firm bold start, which is an amazing firm that’s had overnight success in a way that I think most entrepreneurs can recognize in that Ed had really started his career way before that, in the mid-90s, initially with a New York firm and then another firm called Dawn Treader, where our paths crossed a couple times. In fact, he and I met when he was a VC, and I was at add one, which is the first company that I founded in the internet sector in New York when and really the one of the first enterprise software companies at the time, focused on internet enabled opportunities. Ed then went on to dontretter, where we had the good fortune. At that time, I had raised a firm called Silicon Valley Venture Partners, and we did a deal called live person, which became one of the first multi billion dollar companies to emerge from the New York landscape. And enterprise software. We talked a few times afterwards, sort of thinking about what we wanted to do next. I wanted to focus more on later stage growth. And Ed wanted to really focus on early stage inception investing. And that’s when he launched boldstart. And so, so great to have you on the pod, Ed.
Ed Sim 2:40
Lots of memories, dude, add one. Og, Steve. Steve, by the way, is an OG. I don’t want anyone to underestimate me. He is a builder and entrepreneur. He was probably one of the first kind of OG entrepreneurs doing some b2b stuff in New York, which is kind of weird. You know, back in the 90s, mid 90s —
Steve Brotman 3:00
So consumer-y At the time, right? Yeah, yeah. So commerce, and there’s only 200 of us, I think in total, you could fit us in a very small restaurant, or big, a big-size restaurant, perhaps. And it was a remarkable time. And we all, we all sort of shared the vision that New York could become something much bigger than it was.
Ed Sim 3:23
Yeah, yeah. It’s amazing, by the way. Steve, I remember, we kind of had that Rodney Dangerfield-like, feeling for those old enough to know, you know, to get no respect. And I remember you and I and others would talk about, man, if those West Coast firms would ever pay attention to what was in New York. And it’s kind of funny now, when you run around New York now, which I know that you are there. And by the way, congrats on alpha. You guys have really done a phenomenal job finding a, you know, finding your, your niche, kind of cracking on it. But, man, think about sequoias here, indexes here. You know, everyone is a 16 everyone’s building big offices here. Like Could you have imagined this back in the mid 90s, when you’re trying to raise capital, and everyone wanted you to leave New York and move to California. It’s kind of mind blowing, dude.
Steve Brotman 4:09
The growth of New York is really remarkable. But as you’ve said in prior conversations, this is where the money is. This is where the customers are. And if you think about the genesis of technology, you know, I remember the first couple offices here for Silicon Valley firms. They were downtown, and they’re basically sales offices for Microsoft and Silicon Graphics and Oracle and sideways, right? That was their tech. That was their tech presence was selling into the enterprise. And I think, you know, to a certain extent, you and I said, Hey, New York’s going to be a big place for enterprise software to actually not just buy the software, but originate it. But I never thought, I don’t think you and I ever thought it would have the type of success it’s had, and but it, but it made a lot of sense at the time, and at least it looked pretty good in our pitch decks, right? Like 1/3 of all Fortune 100 companies are based in New York and, et cetera, et cetera. I think. I think we believed it, but in the same way that I think entrepreneurs often forget about is that it’s really and what you and I both discovered is that, in a way, New York is a niche. It’s five or I guess it’s maybe 10% of US ventures at the moment, maybe 15% but it leads to a much wider world.
Ed Sim 5:39
It does. It’s like the gateway —
Steve Brotman 5:41
Which is really and I think as you and I have sort of grown our own careers, and when we started in New York, we’ve expanded to much bigger platforms, and they invest globally. And that’s pretty, pretty interesting. How do you, how do you think about investing now? I mean, I remember investing back in the day where it was, where it was a 10 minute drive, but, but today is that, is that as relevant today, as um, as it was back in the day, pre-Zoom, pre internet.
Ed Sim 6:16
I think for some it is, but for us, it never has been. And I mean, look, when I think about investing now, first of all, I don’t think I’m doing anything different than I used to do. It’s just the nomenclature has changed. You know, when we first did these rounds, Steve, they were called Series A rounds. So you’re out raising a Series A round. There’s no nothing before series A there was no seed round that was like, when we started. Both started 2010 they’re like, four or five seed firms around, and they’re all generalists, and we didn’t want to specialize in enterprise software. And people like, You’re freaking nuts and, and the reason we didn’t have them, yeah, yeah. And the reason, and the reason we did that was not because I’m that smart, it was because the founders are the smartest, right, Steve, and so you follow the founders. And we had exited a bunch of companies, like, GoToMeeting and, you know, green plum, we just excited to EMC, which eventually went public as pivotal. And these founders kept coming back and saying, hey, you know what? There’s this thing called Amazon, EC, two, pre cloud computing. And I think I can actually, you know, start a company and kind of figure out there’s a model for a million dollars. And at the time, as you know, Steve, you had to raise $5 million as an enterprise software company, particularly if you’re building real hardcore software, to figure out if you could even nail it and nail just to build.
Steve Brotman 7:29
You had to buy the deck alphas to even start.
Ed Sim 7:34
Yeah, and so. And you need that. You need the software, and then the rise of open source too. So if you look at the rise of open source and Amazon EC two, and these founders come back saying, I just need a million bucks to nail it, and then I need the real money to scale it. And they said, Look, there’s no one willing to write a small check. And we’re like, geez, maybe I can just and I started writing some personal Angel checks, like, you know, $25-50k checks, nothing big. But then I realized, holy crap, if we could actually, you know, write small checks for these founders who didn’t want to raise a lot of capital at the time and provide enormous value. Perhaps there’s a business, and that’s how both charts started in 2010 and fast forward. The reason why I say it’s not changing, there’s this thing called pre seed that showed up, which was before seed. Then there was seed plus, and there’s Series A, I mean, you kind of know all the nomenclature, but the reality of it is nothing really changed. Steve, when you started at one I was like, I have an idea. I might not even have shipped any software yet, but I need capital. Who do I go to? And I think that’s still the same thing today, except it’s confusing, right? I mean, do I go to a pre seed investor? Well, guess what? A pre seed investor is the investor that is supposed to say, I’m going to invest in two people with an idea and their dog sitting in a loft. But the median age, according to PitchBook, of a company that raises a pre seed round now, is 1-2 years old.
Steve Brotman 8:49
So yeah, yeah, it always struck me that part of the reason there was no seed round was that angels did it. And if angels do it, they’re not really documented. They’re like undocumented investors. They don’t really exist. They don’t exist in PitchBook. You know, institutions don’t recognize them. It’s just like the board. It’s like the border, right? No kidding. Sorry, no, I mean, but AngelList, in a way, has sort of popularized the sector in a way that I don’t think people really realized. Is that, but, but, but, but to your point, back in the day, institutions didn’t really do zero revenue, napkin businesses, particularly in
[continue to page 2]