Michael Ebel

Samsara, ServiceTitan, and Procore Technologies have a combined valuation of $40B+ —and founders with wildly different industry experience. Yet VCs still debate whether it's needed to build great vertical software. As always, my stance is: It depends. The better question is: What type of founder are you, and what's your path to understanding your customers deeply? Some investors are adamant that you must have deep industry experience to build successful vertical software. Others claim outsiders have the advantage. Both camps love to cherry-pick examples that prove their point. But I've been advising and investing in vertical software companies for over two decades, and I think that's enough exposure to confidently conclude that founders of all backgrounds can be successful. Take these 3 examples (Samsara, ServiceTitan, Procore). They're some of the most successful vertical SaaS companies today. Some of the founders come from deep industry experience, but others have a background that would surprise you. → Procore's founders came from construction backgrounds and built a $10B+ company selling to their former industry. They'd lived the pain points they were solving for. → On the opposite end of the spectrum, Samsara's founders had zero experience in trucking or heavy industries. These MIT grads had just sold Meraki to Cisco for a billion dollars and were looking for their next challenge. They picked fleet management and transportation—two industries they knew nothing about. Today, Samsara is worth more than $20B. → Then there's Service Titan, which charted a middle path. The Stanford-educated founders didn't work in the trades themselves, but they grew up watching their parents run HVAC and painting businesses in Southern California. They bonded over their shared background and built a $10B+ company serving those same trades. So it's unreasonable to say that a founder's experience is the determining variable of success. Instead, what all 3 of these stories have in common is founders who deeply understood customer problems and built exceptional products to solve them. Industry outsiders often bring fresh perspectives and aren't constrained by "how things have always been done." Industry insiders have instant credibility and know which problems matter most. Those with adjacent experience can bridge both worlds. As an investor, I back founders regardless of their industry background. What matters most to me is their ability to build, learn rapidly, and maintain fanatical customer obsession. Where do you stand on the industry experience debate? I'd love to hear your thoughts.

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🥾 #bootstrapping as a mindset should be ephemeral, one that requires a deliberate transition away from as a business enters sustained growth Appointing an established auditor is often regarded as a luxury and not part of bootstrapping Audits discipline a business - to be methodical, thorough and deliberate - traits that acquirers often seek in due diligence After all, "What gets inspected, gets respected," Anon We will share the traits of venture businesses sought and respected by MNC acquirers, join us if your business is out of the #bootstrapping mindset #fulfillingpotential #hepmil #oobmil

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VC schedules, and thoughts on being a VC noob. -- VC schedules to know -- Most venture capital firms hold partner meetings on Mondays. This is typically when the investment committee votes on new investments and other key decisions. Savvy founders learn the exact timing and may need to provide additional data over the weekend to stay in motion. It is also well known that many venture capitalists observe a “European summer,” with August often being light or fully off. Similarly, the winter holidays reduce activity across much of December. That said, data from Carta shows a meaningful year-end push to close deals in December, followed by a flurry of activity in January. Founders should be cautious about kicking off fundraising during these slower periods. You do not want a raise to go stale and fall apart. VCs talk to each other, the industry is highly interconnected. -- I’m a mid career Noob! -- I am an “emerging manager,” effectively a new VC, less than three years in. In venture capital, the timeline is long. On my Linkedin you'll see I have two roles at Blitzscaling: Limited Partner means I put money into a fund, but have no decision making ability, and General Partner means I'm actively finding startups, bringing them to the partnership, and funding. As a General Partner, you are often considered an emerging manager for close to a decade, as it takes years for a fund to fully mature and establish a VC track record. Investing is a long game, but the upside can be extraordinary. Fortunately, I entered this role with a positive angel track record from my own bank account, which is often a good idea to have as a VC. When I learn a new VC concept or term, I’m an AI first, I’ll link to my post a few days ago in the comments, I totally live for constant growth and learning, if you’re not growing you’re dying. Fun fact: Many/most start their VC career in their 40s, as they need to have enough tech and biz cycles, a broad enough network, resources, and a platform to stand upon. As we end the year, I'm sharing more career thoughts, and productivity thoughts, rather than industry trends and market maps and frameworks and forecasts. I wrote all of this by hand myself, but used AI to edit some of it.

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Every hire, product feature, and GTM experiment is a capital allocation decision, most teams just don’t call it that. I’m kicking off a 3-part series on capital allocation for founders, operators, and finance leaders with a simple question: ➡️ Will the next $1 you deploy become worth more than $1? Series overview Part 1: defines the core concept + the math Part 2: where capital goes + how to measure whether it’s working Part 3: AIMS framework for communicating allocation decisions to management teams and your board Part 1 (attached here) lays the practical foundation: 🔹 The $1 invested test and ROIIC vs. hurdle rates (scoreboard vs. decision lens) 🔹 A lightweight “investment brief” to evaluate bets (GROW / BUILD / BUY) 🔹 The small metric toolkit that translates finance into operating decisions (NPV / payback / ROIIC / incremental margin) 🔹 Early-stage proxies when DCF inputs are unknowable (burn multiple + revenue quality) 🔹 Operator “vital signs” to spot drift early (profit engine, leverage, cash conversion, optics) Series Roadmap ✔️ This series (Parts 1–3): breadth-first. shared, lightweight framework to define value creation, choose decision-grade metrics, and communicate tradeoffs clearly ✔️ Next series: depth-first. momentum drivers + operational decisions that need near real-time measurement to spot drift early and course-correct fast Read Part 1 here and Part 2 and 3 on substack. Next Series will be out next week. 💰 What’s one bet you’re funding right now, and how will you prove it’s working?

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Just read a piece from the team at Camber Creek portfolio company Proof on the evolving state of authentication…and it hit home. For years I’ve been thinking “passwords are dead,” but also lamenting the difficulty navigating the labyrinthine world of advanced security. This blog lays out exactly what’s replacing passwords in a way that’s practical, not just theoretical. Five methods stood out: - App-based authenticators finally killing SMS (good riddance, SIM-swap nightmares) - Continuous authentication that watches behavior during the session (the “someone stole the cookie but can’t act like you” protection we’ve all been missing) - Adaptive authentication that doesn’t treat grandma on her usual iPad the same as a login from a Tor exit node in a new country - MFA done right (and then taken further with verified digital certificates) - Biometrics with actual liveness + document tying, so it’s not just “a face” but your verified face What really resonated was the reminder that the strongest systems aren’t about piling on more factors; they’re about using the right factor at the right moment. Risk-based, context-aware, and (crucially) user-respecting. I’m biased but Proof’s angle of anchoring everything to high-assurance digital certificates feels like the missing glue. It’s one thing to authenticate someone at login; it’s another to carry that verified identity forward through the entire session, signature, or transaction. This one is worth the read. Link in comments. #venturecapital #cybersecurity #fraud

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I’ve spoken to over 2 dozen MDs at PE firms I can confidently say that the arb of figuring out how to implement Vertical AI at portfolio companies is very real right now It will fundamentally change underwriting for those who can do it predictably and unlock generational returns. Most are aware they need to act. Very few have.

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Boards are supposed to help founders. Over the past 19 years, I've watched many trap them instead. As companies scale, many boards turn from insight to oversight and stop doing what founders actually need: Help making big, hard decisions. Early boards tend to be small, the board members are close to the business and highly invested in it. They argue from first principles. They help founders think. Later-stage boards often look more impressive on paper - they have more independent directors, committees and process. Somewhere along the way, collective problem solving gets replaced with oversight. The board shifts from helping the CEO make better decisions to monitoring decisions that have already been made. Strategy discussions get safer, real debate gets rarer and meetings become more about risk management than judgment. This usually coincides with the introduction of more professional board members. For better or worse, they often optimize for governance, optics, and liability management. That’s their job. But it’s not always what the company needs in moments of real uncertainty. Then, CEOs stop using them as thought partners. That’s a problem. So what should founders do? A few principles that help: • Keep the board as small as you can for as long as you can • Add directors for new insight they bring, not what boxes they check • Treat board seats like senior hires, not trophies • Design meetings for debate rather than reporting • Be explicit about when you want input vs approval Good boards should improve decision-making. If your board isn’t making you think harder, it’s probably not doing its job.

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Founders doing $5M+ don’t lose by picking the wrong channel. They lose by running too many at once. At that stage, complexity is the tax. Every channel can work. The mistake is spreading focus instead of scaling what already converts. The real question isn’t what’s new. It’s what’s predictable. If you had to cut everything but one channel tomorrow, which one survives?

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Most startups sell into verticals. We’re taking over one. Ohanafy is rebuilding the operating system for a $7.6B industry, starting with beverage alcohol, a $1.2b wedge. Legacy players are drowning in disconnected systems: Sales. Ops. Finance. All running on tech that doesn’t talk to itself. The Frankenstein software approach means everything breaks and lags. •⁠ ⁠Fragile integrations •⁠ ⁠Delayed reporting •⁠ ⁠Missed decisions Ohanafy didn’t ask: “What’s the next feature?” But: “What would it take to replace the whole stack?” So they built it: → Native on Salesforce → Multiple tools consolidated into 1 → Customers save 20+ hours/week → Field teams onboard in days, not months → Sales, ops, and finance run from the same screen This isn’t just a product. It’s a platform play. We’re now raising a $3M bridge round to scale faster into enterprise, double down on AI, and shorten our time-to-profitability. If you want to back a vertical category winner, this is the full-scale land grab to look at. DM me to look at the full deck!

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