Bootstrapping an investment bank to $100M+ deal volume
Einar Vollset was an academic with a PhD in Computer Science. Then, he started a YC-backed company, exited, exited again, and "fell into" the M&A space. Now, he's the cofounder of TinySeed and founding partner of Discretion Capital, which does $100M+ in deal volume.
Here's Einar on how he got here. 👇
Falling into it
I have a PhD in Computer Science and I was a professor at Cornell for a couple of years. Then, I sort of just fell into this lifestyle, honestly.
I sold my second business in 2015-16 and then got pulled into doing technical due diligence work for old-school PE firms. One time, I was out to dinner with one of those clients, and someone said, "You know we pay for deal flow." I had no idea what that meant, so he explained, "You know, if you introduce us to someone we end up buying, we'll give you a cut." I now realize this is what buy-side brokers do.
So, I did that a couple of times, and one ended up closing.
Right around then, the larger PE firms started moving down market in the B2B SaaS space — before 2010 or so it was rare for PE to buy SaaS businesses with less than $10M ARR, but they started buying as low as $1M. So, lots of founders that I knew (directly or indirectly) started getting cold inbound offers from PE to sell their business, and I ended up being the go-to guy for advice.
Initially, I'd just give founders my opinion — good offer, crap offer, terrible firm, etc. Then, one time I was chatting with someone and I explained that not only was the offer likely 1-2x lower than what he could get, the PE firm that had made the was notorious for firing all domestic staff and milking profits. He then said, "Okay, thanks. Hey, could you help me find a better offer?"
So I thought, "Yeah, I probably could." And here we are.
Discretion and TinySeed
These days, I'm mostly working on:
Discretion Capital — a bootstrapped investment bank
TinySeed — a fund for mostly bootstrapped founders
When getting started on Discretion, I didn't want to hire a bunch of MBAs, and I couldn't afford PitchBook or other databases of deals and portfolios. So, I built a set of scrapers to keep track of approximately all the PE firms in the world and their portfolios.
Our internal systems are quite a bit more sophisticated now, with AI and things, but the core idea remains: We keep track of who owns what, when they bought it, etc.
Bigger deals
Discretion charges a success fee — a percent of the transaction price. That makes revenue highly variable.
And we grow our revenue by serving more and larger clients. We started out focusing on companies with $1-10M ARR. Now, we say we do $2-20M ARR, but we'll probably have to bump up that top number a bit this year.
Client growth has been via word of mouth. Once you add 300% to someone's initial offer, word gets out.
The last few years, we've done well above $100M in transaction volume yearly.
Educating the market
The biggest challenge is educating founders — particularly technical founders, which make up about 95% of our clients. They're often pretty suspicious of "investment bankers" — or "investment wankers" as one English client memorably referred to us initially.
They often feel like, "Hey, this is something I could just do myself and save the fee." Which is true. They can do it themselves and save the fee. But the problem is that with the market being so opaque and sellers (usually) only ever selling a business once, it's extremely hard to get top dollar if you DIY.
It doesn't feel fair, but that's just the truth.
A technical advantage
Being very technical and not your usual "investment wanker" has been a huge plus for us.
Often, the junior guys tasked with actually doing the work for the kinds of banks we compete with — at least on the upper end of our ARR range — are not very technical and quite often a bit resentful they've been put on such a "small" deal.
Don't be anti-sales
My advice is simple: Don't be anti-sales. And don't be anti-selling-to-enterprises.
It's an incredibly valuable thing to ask yourself, "What can I build that someone would pay $500 (or $5000) a month for?"
What's next?
My goal for the future is to flyfish more.
You can check out discretioncapital.com, email me at [email protected], or watch me argue for fun as @einarvollset on the Twitters.
Leave a Comment
@James whats keeps you going now? After the deal
Really interesting path into M&A.
When you first realized founders were getting systematically bad inbound offers, what made you confident this was a repeatable market problem and not just a few isolated cases?
Was there a moment where volume or pattern made it obvious?
Do you have any suggestions on this, maybe based on your own personal needs or what your clients say?
This is a fascinating story—especially how the early deal flow came from relationships rather than traditional marketing.
I’m curious: at what point did you feel confident enough in the pipeline to stop saying yes to every opportunity and start being selective?
Would love to hear how that transition happened.
Really well written!! Thanks
Thanks for sharing this — it was a really thoughtful breakdown of a path that most founders don’t talk about openly.
Bootstrapping an investment bank and driving $100M+ in deal volume is impressive not just because of the numbers but because it highlights a mindset shift that many makers overlook:
Product + Sales Matter Equally
Building a useful data system or tech stack is necessary, but it doesn’t replace the fundamentals of sales and client relationships. Educating the market and earning trust — especially in a space where most founders are skeptical of “investment bankers” — is a big differentiator.
Technical Credibility Is Real Leverage
In markets that are traditionally opaque (like M&A), having actual domain knowledge and technical depth can lower barriers and build trust faster than slick branding alone.
Bootstrapping Doesn’t Mean Anti-Growth
It’s good to see a real example where scaling comes from consistent client success and word of mouth rather than chasing outside capital — which echoes why many founders choose to stay independent in the first place.
Advice for Other Founders
For anyone building something in a niche or skeptical market: don’t be afraid to lean into sales and education. Open communication about value, process, and outcomes helps reduce friction on both sides of a transaction.
Overall, this feels like a strong case study for how deep domain understanding and execution fundamentals — not just “tech” alone — can unlock real, sustainable volume in a traditionally relationship-driven space.
Great insights, thanks for sharing!
This works because selling a company is a one-time, high-stakes, opaque decision.
The buyer has reps. The seller doesn’t.
Technical credibility + market visibility collapses that asymmetry.
The tools matter less than the judgment built from seeing hundreds of deals.
That’s what founders actually pay for.
Really liked this breakdown. The point about consistency over hacks is underrated. Curious—what was the hardest part for you in the early days?
I enjoyed reading this, particularly the part about falling into things, not chasing them, or some larger-than-life plan. ~
What I found interesting is the positioning + trust raised much of the leverage rather than the scale. You didn’t compete with banks; you focused on helping founders feel understood while using tech depth to reduce friction on either side. Those creatures are rare and compounding.
A couple of patterns from here match what I’ve seen elsewhere.
A person who explains a market clearly (especially when it is opaque) becomes its default.
Undetected performance edge: not as “cool tech”, it is faster answers, cleaner diligence, fewer surprises.
Early acceptance of smaller, out-of-the-box agreements that leverage word of mouth to do the rest.
Don't be anti-sales is also a good point. It’s easy to romanticize builders who hate selling, but maybe instead you can change your framing: what could I build that someone would happily pay $5k/month for? it has a really grounding filter
I’m curious how you think about bottlenecks today deal flow, your own bandwidth, and/or maintaining quality as the volume grows? It appears to be a commercial enterprise in which the limitations change in engaging (and non-linear) methods.
Really interesting transition. I’m building a marketplace now and seeing how much of success comes from trust and relationships rather than pure tech. Did you find deal sourcing or execution harder to systematize at scale?
This resonates. I am seeing the same thing while building-once you move past the core tech, trust and relationships start dominating everything. Curious how you are thinking about that on your marketplace.
I'd never heard of TinySeed until I read this. It looks great!
Thank you for your sharing.
Haha, I used to be in the same industry, and most ofthe things you said are real
Really interesting story—bootstrapping an M&A firm by building proprietary data scrapers and focusing on underserved SaaS founders is a strong contrarian wedge.
The takeaway on “don’t be anti-sales” and educating a skeptical market is gold for indie founders who underestimate distribution and deal-making.
Well said. THe contrarian wedge is not just the data scrapers-its understanding founders and the market mechanics better than traditional players. The "dont be anti-sales" point really ties it together: distribution and deal execution are the real leverage.