Nov 30, 2015 · 25m · 20vc
20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews Ed Sim, Founding Partner at BoldStart Ventures, about early-stage enterprise SaaS investing and capital efficiency. Sim shares insights on evaluating pre-revenue software startups, changing VC market dynamics, and the evolving playbook for scaling modern B2B tech companies.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 27.7% of the talking time here. How this is scored →
Harry as informed peer 3.0 Guest teaching 3.7 Guest disagreement 1.0 Harry pushing back 1.2
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 18:06 Ed dismisses crowdfunding threat
Ed firmly rejects the premise that AngelList poses a threat to traditional seed VCs, emphasizing that venture remains inherently relationship-driven.
Hardest push from Harry ▶ 18:54 Harry presses on AngelList future normHarry refuses to accept Ed's initial brush-off regarding AngelList, challenging him on what happens if the next generation of founders normalizes public crowdfunding.
Biggest teaching moment ▶ 14:35 Ed reframes market sizing metricsEd corrects standard market sizing assumptions by explaining that if a seed startup relies on existing industry analyst reports, it is usually a bad sign for early stage innovation.
Harry holds his own ▶ 6:02 Harry frames early enterprise capital efficiencyHarry articulates the prevalent industry belief regarding enterprise capital intensity, setting up Ed to detail the macroeconomic cloud shift.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Ed Sim's Venture Capital Career and Launching BoldStart | 2 | 3 | 0 | 0 | Harry introduces Ed Sim and prompts him to share his background launching Dawn Treader and BoldStart. Ed explains his history in early-stage enterprise investing without any tension or pushback. | |
| Capital Efficiency and the SaaSification of Enterprise | 3 | 4 | 1 | 1 | Harry asks about the misconception surrounding early enterprise capital needs. Ed educates the host on how the ASP model required high infrastructure capital compared to today's cloud-enabled efficiency. | |
| Navigating Early Stage Enterprise Metrics and Deal Sourcing | 3 | 5 | 1 | 1 | Harry asks how enterprise VCs evaluate deals without metrics. Ed colorfully notes that enterprise is hard but explains that core enterprise pain points recycle over decades. | |
| Market Sizing, Micro VCs, and the SaaS Playbook | 3 | 4 | 1 | 1 | Harry inquires about market size requirements for seed investments. Ed reframes the topic, explaining that analyst reports are useless at seed and that portfolio construction relies on fund-returning upside. | |
| Venture Stratification, AngelList, and the Micro Enterprise | 4 | 4 | 2 | 3 | Harry pushes Ed on whether AngelList and crowdfunding could disintermediate seed VCs. Ed counters that venture remains a relationship business and that private syndicates prefer discretion. | |
| Quick Fire Round with Ed Sim | 3 | 2 | 1 | 1 | Harry runs through rapid-fire questions covering regional valuation differences, favorite media, and current enterprise trends. Ed outlines his preference for sub-10 million valuations versus West Coast inflation. |
Statements from this episode (18)
Ed Sim raised $1M for Boldstart Fund I, making 10 seed investments
“I just took a million dollars in and made 10 investments of about a 100,000 a pop.”
Boldstart Fund I pre-money valuations never exceeded $6M in 2010
“I think in fund one, I don't think we paid higher than a five, Million dollar pre-money for any of our investments. Five or six.”
Boldstart Ventures sold four Fund I companies within two years of launch
“We built that portfolio up in 2010, and by 2012, we had sold, ah, I think four of our companies.”
Pre-cloud enterprise startups required $4M to $5M Series A rounds
“A traditional way of building an enterprise startup would usually require at least four or five million dollars in an A round up, up until the point that, The newer entrepreneurs took advantage of the cloud and open source.”
LivePerson spent $20M of its $30M raised building proprietary infrastructure
“A company like LivePerson, we probably raised, you know, over thirty million dollars in about 12 months. And 20 of that went to build our infrastructure because we wanted to build for success, and you needed to build a platform that could scale.”
BoldStart Ventures refuses to invest in single-founder startups
“Well, I, we never liked single co-founder, co-founded companies or single founders, number one.”
Five of BoldStart's last six investments were repeat entrepreneurs
“We funded, I think the last five or six companies we funded, five of them were repeat entrepreneurs who have built, you know, and scaled companies before”
BoldStart Ventures requires founders to be engineers actively building product
“And secondly, they have to be engineers. Engineers, Building product. That's really important.”
Enterprise founders achieve repeatable success easier than consumer entrepreneurs
“And in consumer, I think it's harder to be a repeat consumer entrepreneur, right? Because you typically start an app, you know, let's say, and launch that thing, and then you try to start another one, but you can't bring that same customer base over. You've go…”
BoldStart receives 75% of its deal flow from its founder network
“I mean, I think we've tracked that about 75% of our flow comes from founders, whether they be founders that we funded before, you know, their VPs, The engineers that work there, or even, you know, from founders in our existing portfolio who are referring their…”
Seed startups relying on analyst reports for market sizing are uninvestable
“If you have an analyst report to kind of show us, then it's probably not worth investing in, you know, at the seed stage.”
Micro-VC funds grew from nearly zero in 2010 to 400 by 2015
“When I started this in 2010, I think one of the only micro VCs was Jeff Clavier, soft tech. ... Since that time, I think there's 350 or 400 now, quote unquote, micro VCs.”
Modern SaaS scales via marketing and inside sales, not field reps
“Instead of building a huge regional direct sales force, you know, Today you may bring on a marketing person to be a lead generation machine, right? And then you have built an inside sales force to kind of, you know, follow up on those leads, and then you bring…”
Developers increasingly drive enterprise software purchasing decisions bottom-up
“I think developers are increasingly wielding more and more power in the enterprise these days, and it's one of those things where they're, you know, coding or develop, or using a new technology, they'll download it, or they'll try a free version, then they'll …”
Legacy enterprise IT will be replaced by micro-enterprise architectures
“I think the whole monolithic IT infrastructure is getting turned upside down. I like to think of the world as becoming You know, I almost call it the micro enterprise, right? Instead of kind of buying these monolithic, five million dollar, ten million dollar s…”
New York seed valuations are consistently lower than Silicon Valley
“I think that the New York valuations tend to be a little lower than the Valley.”
BoldStart Ventures strictly keeps seed valuation caps below $10M
“We'll just say sub 10, and it could range from much lower to, you know, upper, up on the upper range. It depends on who the founders are, what their background is, and, you know, and how much they're raising.”
AI will infiltrate every enterprise software category within five years
“I think I'm seeing a lot of kind of AI, not AI platforms, but AI being infiltrated across every segment of enterprise software. And I'm also seeing a lot of stuff where messaging is going from consumers to the enterprise as well. Messaging meaning you know, al…”