In the latest episode of Raiser’s Edge, Kevin Bennett, who has raised over $200M for his companies HomeZen, Caribou, and now Further, borrows this idea to describe how building a relationship with investors actually works. For Kevin, it’s about small, often seemingly unremarkable deposits — showing up on time, doing what you said you’d do, telling someone something true before they ask — that accumulate to build the confidence an investor needs to fund something that doesn’t sell itself on the numbers alone. He calls it the “trust dividend”, and it’s a big part of how he’s been able to achieve success in often unfavorable categories, including achieving unicorn status for his company Caribou.

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Here are some of my takeaways from my conversation with Kevin.

1. Admitting what you don’t know is actually a sign of strength.

I asked Kevin how he learned to fundraise. His answer started where you’d expect — learn by doing, more of what works, less of what doesn’t — but the real insight was one level down: the most important skill isn’t any individual fundraising tactic, it’s “learning how to learn.” Being perceptive enough to notice what’s actually resonating, and asking the right questions to find out.

The specific move he named is almost embarrassingly simple: when you don’t know something, say so. Founders, especially insecure ones, default to performing certainty and acting like they have an answer for everything. Kevin’s read is that this backfires. Transparency about your own thinking, including the gaps in it, is what actually builds investor confidence, because it signals you’re giving them the full story instead of a curated one. The dividend isn’t paid by looking like you have it all figured out. It’s paid by being honest about the parts you don’t.

2. Find the right dance partner.

Kevin told me about pitching a high-profile investor years ago. A few good conversations, even dinner out in the Valley to talk through the business. Then it just stopped without a real explanation. Weeks later, the feedback came back through a different investor: the guy had spent the whole night needling him, hoping to provoke him into wanting to throw a punch. Kevin never took the bait. That, somehow, was the problem.

Kevin’s take on it: that investor was looking for a fight club conversation, Kevin was looking for a trust dividend conversation. Two completely different ways of building a relationship — neither one wrong on its own, but if you’re not the same kind of investor or founder, no amount of chemistry closes that gap. Early in his career, he said, this kind of pass from an investor made no sense to him; he assumed it reflected on his business. In hindsight, it had nothing to do with the business and everything to do with fit. He didn’t lose that investor. He found out, for free, that they were never going to be the right partner anyway.

3. Learn how they weather the storm.

Kevin has a go-to question when he’s getting to know someone: what’s the hardest thing you’ve ever done, personally or professionally? He says people take about half a second to decide whether they trust you — and if they do, the answer is almost always personal, because the hardest thing anyone’s done usually is.

What he’s actually listening for isn’t the story itself. It’s the narrative structure underneath it. Kevin hopes to hear an answer that sounds less about and, in his words, more like “this happened, and here’s what I did about it, and here’s what I learned.” Agency, not just hardship. Startups are hard in a specific, recurring way, and Kevin’s bet is that people who’ve already metabolized one hard thing into a story about their own agency are the ones who’ll be good at the next one. It’s a qualifying question and a trust-building one at the same time — the asking is itself a small risk, and the answering is a bigger one, and both sides walk away knowing more than they did sixty seconds earlier.

Kevin’s closing advice to founders was to be 100% the best version of yourself — not 98%, not 99%. It’s the kind of line that could risk sounding like an inspirational poster if Kevin wasn’t such an exemplar of putting that advice into action. Everything in the conversation is really just a description of what that looks like in practice: relationship over transaction, honesty over performed certainty, every touch point treated as real instead of incidental.

None of it is a cheat code, or a secret hack. That might be the point. The dividend doesn’t pay out because you found the trick. It pays out because you kept making the deposit when it would have been easier not to.

For more wisdom from top founders like Kevin, and my takeaways on every interview from Raiser’s Edge subscribe here on Substack. And don’t forget to follow us on Spotify and Apple Podcasts to make sure you don’t miss an episode!

Stay sharp,

Ben

When it comes to how to succeed at fundraising, Sean is relentlessly focused on understanding what’s actually going through an investor’s head — before, during, and after the meeting. That’s led to his repeated success, even when the market was at its worst and companies all around him were closing their doors.

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Here’s what Sean’s strategy looks like in practice:

1. Be remembered.

Investors see five or six pitches a day. And most of them end quietly, with a polite thank-you, a vague follow-up offer, and then out the door. What Sean argues for is instead ending with a bang that sparks imagination and excitement - a hook they’ll still remember at the end of the week. You want them walking out of that room thinking about the potential of what you’re building, not just cataloguing the facts of it: What does the world look like if this works? What’s the size of the opportunity they’d be passing on?

Investors will rarely be more passionate than you are, so let your own excitement come through. That’s what gets you a second meeting.

2. Filter for conviction, not convenience.

Founders often make it “easy” for investors, jumping through hoops to meet on inconvenient terms and wasting cycles on lukewarm leads. Sean’s play? Add friction: let investors come to you, meet on your turf, and watch who puts in the effort. The ones who opt in despite the friction are already showing conviction. They’re the ones who will fight for your company.

3. Know their bias.

Every investor who sits across from you has already formed biases based on your space, your category, who referred you, what’s in their portfolio, what bets they’ve made before that worked or didn’t. Sean’s point is that a lot of founders try to overcome that in the room.

The smarter move is to figure it out before you ever schedule the meeting: Who’s already fishing in your pond? Who’s had a win that looks like what you’re building? Who’s been burned by something adjacent and won’t go near it again? That’s the research that actually moves the needle — and most founders skip it entirely.

4. Give the raise full focus.

Don’t fool yourself into thinking you can fundraise “on the side.” If you’re raising, act like it. Treat it as a 3-6 month full-time blitz, not a side project. The founders who try to juggle everything inevitably stretch the process, adding pressure and risking both the business and the raise. Block the time, do the prep, and expect it to take longer than your best-case estimate. Fundraising IS your job now - so plan accordingly.

For more wisdom from Sean, you can listen to his podcast, The Startup Help Desk, and subscribe to his newsletter, The Breaking Point by signing up below. Both are excellent resources for founders and fundraisers looking to get their company through the next round, and to take it to the next level.

The Breaking Point

Advice for leaders on how to make better business decisions.

By Sean Byrnes

If you want to hear from more world-class founders like Sean on what actually moves the needle in fundraising, follow Raiser’s Edge on YouTube, Spotify, and Apple Podcasts. And if you want my top takeaways, frameworks, and stories from each episode delivered straight to your inbox, sign up for our Substack—you’ll get practical wisdom the minute each episode drops.

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Ben

Tushar Garg, founder and CEO of Flyhomes and my guest on episode 10 of Raiser’s Edge, walked right into that nightmare. He was starting a critical fundraise, the kind that determines survival, when his co-founder was suddenly hit by a drunk driver—severely injured, out for a year, future uncertain. Meanwhile, his own newborn was also in the hospital. Tushar was literally sleeping in hospital rooms, splitting time between crises and flying out to give pitches and save the company. No playbook covers these moments, but surviving—and growing—through them sets apart those who make it from those who don’t.

Every founder I’ve worked with has lived through highs and lows. Tushar Garg has also lived through some near-unthinkables. Tushar isn’t just another entrepreneur with a $200M+ track record. He’s proof in action of how relationship-driven funding can be the edge that keeps your company alive when the market—or your luck—turns.

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Here are my biggest insights from my conversation with Tushat:

1. Don’t mistake fast fundraising for a strong foundation.

Tushar had the dream start: first check in 30 minutes, Series A from a Tier-1, sky-high growth. But that early ease masked a big risk—he hadn’t built a broad base of deep investor relationships. When crises hit, there was no deep bench of allies to turn to. His story is a caution: easy money isn’t a substitute for “quietly tending your garden” over the years. Relationships are the real reserve capital; you can’t afford to ignore them.

2. Vulnerability is a power move.

Founders obsess over projecting confidence. But what stood out from Tushar was his radical transparency—especially when things got tough. In moments of crisis, he didn’t try to spin reality or stay “on script” with investors or employees. He was upfront about losses, difficulties, and his own vulnerability. The payoff? He proved his resilience to his founders, and it built deeper trust and loyalty with his investors. Most founders shy away from that level of honesty, but Tushar’s example proves it’s not just good ethics—it’s a competitive advantage.

3. Trust is the currency that counts.

Tushar said it best: “Trust is your currency. Trust is the thing that compounds over many, many years and it’s too easy to lose that”(25:11). The pandemic market boom turned into a brutal reckoning for real estate companies, with many of them shutting their doors. Tushar moved fast and refined his company, shifting its focus to wholesale and B2B. But even bold moves only work if you have the right people—on your board and your cap table—who will back decisive and sometimes painful shifts. When fundraising gets hard and numbers alone don’t impress, it’s the long-term trust you’ve built, across every interaction (even with people who say “no”), that gives you the only real edge. Tushar’s seed investor stepped up a decade later to save the company in its hardest hour; that compounding trust is something no deck, no metric, no hot market can replicate.

Fundraising isn’t a game of sprints or luck. It’s the patient, persistent compounding of trust, built one authentic interaction at a time, across seasons of boom and bust. That’s the only thing you can reliably bank on, and Tushar proves it’s the edge that keeps you in the game.

Want to unlock more behind-the-scenes insights from top fundraisers? Sign up here on Substack to get my takeaways and practical strategies delivered every week when new episodes drop. Join us and stack the deck for your next capital raise.

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Ben

Stefan has built and exited companies, invested in unicorns, and just closed a preemptive $8M seed round for his latest startup before even introducing the product. But what stands out most isn’t his tactics—it’s the character and craft behind his capital raising, and the way he strives to be a “presidential” founder.

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Here are a few of my favorite takeaways from my conversation with Stefan that got me thinking about what real capital leadership looks like:

1. Magnetism is a skill.

Stefan talks about the “presidential founder”—a leader who isn’t just technically sharp, but knows how to attract capital and people to their cause. Presidential founders steer the discussion, ask pointed questions (“What does your fund care most about in this round?”), and listen hard for real signals. It’s not about dominating the room; it’s about showing you’re at the helm, willing to change course boldly based on new information, and treating the investor as a real partner.

But the presidential founder isn’t just a company spokesperson. They’re someone whose clarity, drive, and communication inspires conviction at every level. For Stefan, fundraising is proof of how well you’ll recruit top talent, close mission-critical customers, and rally a board to your cause. So if you can’t prove to investors that you’re able to pull people into your vision during your pitch, you’re exposing that you’re not ready for the marathon that is building enduring companies. Becoming a presidential founder is a concrete skill, not just a personality “type”—and it’s one every founder can (and must) develop.

2. Find a kingpin.

A lot of founders obsess over valuation. But Stefan points out that the composition of your cap table from early on sends powerful clues about the quality and trajectory of your company. Stefan’s playbook: Secure your “kingpin” investor, the investor who others know and trust enough to follow. The ability to enroll high-signal, concentrated investors in the early stages builds confidence and generates momentum and so when your cap table has true believers with a track record, it says as much about you as it does about them. Presidential founders orchestrate these early alliances with intention—each check is more than money; it’s capital endorsement.

3. Reset the room — even if it’s awkward.

Being a presidential founder doesn’t mean your pitches are always flawless. In fact, Stefan says that sometimes the greatest differentiator is the courage to call a timeout, admit something isn’t landing, and reframe the conversation—even if it’s in front of a legendary investor. That willingness to take the wheel, redirect, and risk embarrassment is a rare skill. Wishful thinking and excessive politeness won’t build consensus (or close rounds). Sometimes the capital advantage goes to the founder who’s willing to pause, pivot, and have a slightly uncomfortable conversation.

Stefan’s approach to capital is about more than closing a round—it’s about embodying the kind of leadership that draws the best people, investors, and opportunities to you. Becoming a presidential founder is about your presence, your decisions, and your ability to forge conviction again and again.

Want more insights and stories on raising like a presidential founder? Subscribe to Raiser’s Edge here on Substack for fresh takes from the founders and funders who set the bar, and follow us on Spotify and Apple Podcasts to make sure you don’t miss an episode

Stay sharp,

Ben

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In our conversation, David shared a masterclass in both the mindset and mechanics of winning over investors. Here are some of my biggest takeaways:

1. Storytelling is the core fundraising skill - and it’s learnable.

From my discussion with David, it’s clear: neither data nor vision works in a vacuum. Great fundraisers, those who get the yeses from top-tier funds, are expert storytellers, blending data and vision together to paint a picture that VCs can’t resist.

David wasn’t always a natural; in fact, at the start of his career, he was terrified at public speaking altogether. But as I’ve found over and over again through this project, for the best founders, improvement isn’t an occasional mindset—it’s obsessive, relentless practice. Through countless reps, tight feedback loops, and relentless self-improvement David was able to strengthen his storytelling skill, and use it to win over more VCs more than raw intellect ever could.

If you're a founder with weak storytelling skills (and most founders are)—what are you doing to fix it? It may be what’s standing between your company and that capital advantage it needs to survive.

2. Tell a “fundmaker” story.

At an early-stage VC meeting for BetterCloud with Sequoia, David didn't even get a chance to sit down before the legendary Doug Leone brushed him off: "This is not a big company — and I'm not interested." It was brutal — but it also rewired David's entire approach for the better.

Venture investors today are looking intensively for fundmakers – those rare companies that perform so well, the gains on that investment alone make the returns for the entire fund. That may mean a 50X return or more. David quickly learned that if he didn’t frame his company as a groundbreaking fundmaker, he wasn’t just failing to impress - he was just wasting VCs’ (and his own) time.

But a big vision isn’t anywhere near enough. What separates the founders who close from those who don't is the ability to connect that fundmaker vision to operational reality, showing not just where you're going, but exactly how you're getting there, step by step. Early on, wanting to tell that fundmaker story that VCs look for, David fell into the trap of overhyping; but when investors started to call his bluff, he realized the real edge was pairing that vision with credibility. Investors keep notes (sometimes for years)—and if you become the founder who not only dreams big but quietly, reliably hits (and beats) their own milestones, the dynamic shifts. This is what turns curiosity into real interest, and interest into FOMO.

3. A pitch isn’t a series of monologues - it’s a back and forth conversation.

It’s a common founder mistake: you get feedback, you nod (sometimes without even understanding what the VC is asking for), you leave, but you don’t push for specifics. David hammered home the importance of flipping from passive to active—asking precisely what “traction” means to that VC, triangulating multiple answers, then getting your company laser-focused on hitting that goal. The real pros don’t just say “thank you for your time”; they treat meetings as discovery. If you don’t ask, you’re operating blind, and you’re missing important data on how to secure that term sheet and strengthen your company.

Everyone hopes for the magic deck or perfect intro that cracks open their round. But David’s journey reminded me (and I see this in all the best founders): fundraising is an obsessive, relentless practice built off of constant re-tuning. The capital advantage comes not from being perfect, but from improving faster than the competition, and playing your side of the table as actively as any investor.

If these kinds of tactical, tested insights help you on your fundraising journey, I’d love to keep sharing them with you. Sign up here for our weekly emails every time a new episode drops, and follow us on Apple Podcasts and Spotify.

Let’s raise smarter, together.

Stay sharp,

Ben

These top fundraisers treat every investor meeting, every piece of feedback, and even every “no” as data. They excel at systematically converting that data into iteration — learning from it and using it as a tool to speed up their velocity of improvement and maximize the success of their raise and their company.

Omar Tawakol, my guest on this episode of Raiser’s Edge, is a pro at this. As the CEO and co-founder of BlueKai, Voicea, and now Rembrand, Omar’s journey spans over $100M raised, multiple strategic M&As with giants like Cisco and Oracle, and nearly constant curiosity and iteration.

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Here are a few insider insights from my conversation with Omar that I think every founder should have in their toolkit:

1. Great Founders Chase the Hard Truths

One of the most remarkable things I saw in my conversation with Omar is his relentless commitment to discovering the actual truth behind his business—no matter how uncomfortable the process. Like all the best founders, instead of trying to persuade or ignore investor pushback, Omar sees those moments as opportunities to uncover what’s real: “Always, always seek the truth. Do not be blinded by drinking your own Kool-Aid...humility is going to allow you to surround yourself with people who are going to challenge you and they’re going to point out the things you don’t see.” By not being afraid to put his timing, thesis, and assumptions to the test, Omar has made his companies more resilient over and over again.

2. Don’t be a Stranger

Once the fundraising process officially starts, the window is narrow by design. Momentum matters, and FOMO only builds when the timeline is tight and intentional. You don’t have room for 40 “maybes,” endless coffee meetings, or customer references taking dozens of calls.

That’s why Omar insists on using the time in between rounds wisely. He explains that the best founders don’t go from total silence to a sudden fundraising blitz. They spend time between rounds finding their target VCs, testing their pitch, pressure-checking timing, and getting honest feedback from trusted investors — not just to soft-pitch and build confidence, but to genuinely listen to investors’ perspectives and questions and sharpen their thesis. I like to call this “pre-heating the oven” on your raise - warming up your market and your pitch so that when the clock starts, you can hit the ground running.

3. Continuous Learning with an Outlook of “Perpetual Beta”

But Omar’s philosophy of continuous learning, iteration, and improvement goes further than just feedback from his investors. Omar explains that if he could have any superpower it would be “the ability to mimic other people’s superpowers”. He’s like a sponge, operating in, to quote Phillip Tetlock, “perpetual beta”, constantly learning from what the CEOs around him are doing. This attitude extends not only to the leaders of the companies he interacts with through his M&As, but to his direct competitors too - he doesn’t see their success as a threat, but as something he can use to achieve his own edge. He looks at the world around him with curiosity and openness, looking not only at veteran founders for mentorship, but also laterally.

Omar’s playbook is more than tactics—it’s a philosophy: relentless focus, strategic relationships, and a constant hunger to learn, even from the hardest conversations. These are the principles that have helped Omar Tawakol build and exit category-defining companies even in the toughest fundraising environments—and they are replicable for anyone raising capital today.

Want more wisdom from top fundraisers and founders? Subscribe to Raiser’s Edge on YouTube, Spotify, or Apple Podcasts. And if you want actionable strategies and behind-the-scenes breakdowns like this delivered straight to your inbox, subscribe here on Substack for my takeaways from every episode!

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Ben

In our discussion, Greg revealed his radically strategic approach to fundraising—and how having survived the hard times where he had to be “a stone cold killer” allows him to look back with wisdom, empathy, and humility now.

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Here are some of the insights from my conversation with Greg:

1. Fundraising Is a Race—And You’re the Driver

Greg compares founders to Formula 1 drivers—coming into corners at life-or-death speed, with only seconds to make decisions. And that speed and control also extends to the raise. He taught me the value of going all in when you’re raising: compress your raise into just two or three weeks of focused, relentless momentum. If you try to stretch a raise out over months, you lose that heat and urgent energy that makes investors lean in, and you waste valuable time that should be focused on building and strengthening the business. Greg lines up all his meetings for a tight window, not just for efficiency—but because that’s the only way you turn a spark into a fire.

2. You’re Not Selling an Egg. You’re Selling the Golden Goose.

One of my favorite analogies from Greg: your investors aren’t buying a golden egg - they’re buying the golden goose. Founders often obsess about the brilliance of their product—the “egg”—when investors are buying a system, a team, a company, a way to repeatedly produce outcomes—the “goose.” In his pitches, Greg reframes his founder story, his team, and his company as a machine that creates great products, shifting from “here’s what I built” to “here’s the engine I built for creating value—again and again.” That’s the insight investors actually bet their careers on – and it tells a story of repeatability that makes the founder themselves backable.

3. The Most Expensive Mistake Is Choosing the Wrong Investor

Greg has lived both the pain of “painfully dilutive” rounds, and the pain of choosing the wrong board members for his companies. His lesson: it’s always worth a compromise on valuation to bring in the right investor. You’re not just picking a check—you’re picking a co-pilot for the wildest ride of your life. Optimize for alignment and trust as the first priority.

4. Hard Work Now Allows Empathy Later

Greg’s final wisdom is as honest as it gets: Early on, you need to be tough, compartmentalize, and protect your company’s future at all costs. But as you grow, your effectiveness as a leader—and fundraiser—comes down to your ability to empathize with your colleagues and investors who took the journey with you. After years in the trenches, Greg has learned that the people matter more than the products - and that empathy makes him a better fundraiser.

Greg’s playbook is a reminder: capital advantage comes not from a magic phrase or pitch deck template, but from the relentless practice of being focused, being relentless, and caring about every relationship—not just the outcome they produce.

Make sure you don’t miss our next conversation with an outstanding founder - subscribe to Raiser’s Edge on Spotify and Apple Podcasts. And to get reflections from my conversations with extraordinary founders like Greg, subscribe to Raiser’s Edge here on Substack.

Stay sharp,

Ben

When my longtime friend & venture investor Gus Tai suggested interviewing Evan Kaplan for this podcast, it was a no-brainer.

As CEO of Aventail, iPass, and InfluxData, he’s raised over $400. But more importantly, he has survived countless market peaks and valleys—not to mention near-death experiences—with incredible resilience. Evan was one of the first people I asked for advice back when I was raising my own first rounds, and he’s coached so many other founders through their own tough fundraising situations.

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Here are some of the key insights I took away from my conversation with Evan, that every entrepreneur can learn from:

1. Know how your investor gets paid.

Most founders never learn the nuts and bolts of venture capital mechanics. Evan emphasized just how important it is to learn what’s happening behind the scenes for your potential investor—not just what they care about, but literally the structure and economics behind their fund. Where are they in their fund lifecycle? What returns do you need to hit to be “worth their attention”? What do they need to prove to their LP’s to raise their own next fund? If you want to get them on your cap table, get curious and ask them about their own business—how they think, what excites them, and how they structure their day-to-day decisions.

Most entrepreneurs wouldn’t even think of extending that kind of empathy to an investor. But Evan shows how it leads to a much better understanding of the investor and what makes them tick—and gives you intel to gain a capital advantage.

2. Action speaks louder than words.

There are dozens of moments when the ball is in the investor’s court in the lead up to a venture round, and any one of them can be a show-stopper. Evan tracks who delivers and who delays on these steps, separating out the investors who are truly committed to their partnership from the ones who will inevitably become roadblocks for the company. In a world filled with gratuitous happy talk and unexplained ghosting, Evan uses follow-through as his signal to forecast honest partnership and future success.

3. Building a relationship isn’t optional—it’s the whole point.

Early in our conversation, I asked Evan whether fundraising is a relationship or a transaction, and his response was quick and unwavering: “Has to be a relationship.” Fundraising is much more than securing capital—it’s laying the groundwork for your company’s future partnerships, board dynamics, and strategies. The investors you bring on will be in the trenches with you, and how you build that early relationship sets the tone for years (and sometimes entire company lifecycles) ahead.

Evan’s lessons are battle-tested, and he has the receipts – and the scars – to prove them. For anyone in the thick of it, feeling run down by the process, he reminds us that at the end of the day, the best thing you can do is also the simplest thing: Drop the bravado and show up with your full self.

Want more fundraising wisdom? Subscribe to Raiser’s Edge on YouTube, Spotify, and Apple Podcasts. Every other week, I interview only the most extraordinary founders and fundraisers to dig deep on what actually works. And for more behind-the-scenes takeaways like these, subscribe here on Substack and get every episode drop, along with exclusive insights, sent straight to your inbox.

Stay sharp,

Ben

In this episode of Raiser’s Edge, I sat down with David Shim, who has mastered the fundraising game as co-founder and CEO of Placed (acquired by Snapchat for $200M), CEO of Foursquare, and now, Read.ai, one of the fastest-growing productivity AI solutions on the market. David has been through both fundraising hot streaks and brutally tough environments, and his crafted, deliberate approach has helped him build a capital advantage and raise over $245M. His secret? He takes a very deliberate approach to engineering his fundraise to meet the market.

Here are some of my takeaways from our conversation.

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1. Design your company to be investable before you raise at all.

Too many founders overplay vision. It’s tempting to rush out and shop your story, but David Shim is methodical about waiting to raise until the company truly earns capital. David makes it clear that deep-pocketed investors (and their analytics teams) already benchmark you against your sector, competitors, and growth rates, often before you even meet. His advice: resist pitching until you have the numbers. When your retention or run rate hockey sticks, the capital will come to you. When the market is cold, obsess over the story, but never at the expense of delivering product metrics that speak for themselves. Investors are pattern matchers—so show up with all the right signals.

2. Don’t chase trends—control what you can.

There’s a perennial temptation to pivot into whatever sector is “hot.” David’s seen the cycles, from crypto and NFTs to AI—but he’s adamant: don’t burn precious runway chasing flavors-of-the-month. Instead, build where you have craft, team, story, and the ability to create real traction. “Timing is the number one factor for startup success,” he told me (see this Ted Talk from Bill Gross for more wisdom on this topic), but the only way to be ready for luck is to have a fundable business—and runway to wait for your window.

3. Practice makes perfect.

David emphasizes practicing your pitch—like “Shark Tank,” not improv. During his tougher fundraises, he connected with 50, even 100 investors, learning that most entrepreneurs let storytelling slide and just wing it. He pushed for objective feedback—sometimes proactively chasing down rejected investors with, “What didn’t you like?” and a willingness to listen rather than defend. Every “no” is actionable data, and by collecting these insights, you iterate toward a more fundable story.

David’s journey reminds me: the best founders aren’t just capitalizing on timing; they’re running disciplined, data-driven, and never complacent processes – and they are hyper conscious of what it takes to earn investor demand.

Want more practical, unconventional wisdom from top founders and fundraising experts? Subscribe to Raiser’s Edge on YouTube, Spotify, and Apple Podcasts. And for behind-the-scenes takes, actionable strategies, and fresh insights delivered to your inbox, sign up right here for our bi-weekly emails on Substack.

Stay sharp,

Ben

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Here’s what I learned from our conversation:

1. Know your weaknesses, and face them head on.

Russ is adamant: founders must have the most honest, unfiltered assessment of their business—strengths AND weaknesses—long before they send a deck to an investor’s inbox. If you’re “prettifying” your business for the pitch without actually solving the issues you’re disguising, you are not ready. The best fundraising starts with deep reflection about what’s actually working and what’s not. That honesty carries through the fundraise and is what investors trust most.

And if fundraising is impossibly hard, something’s off. It’s not just a matter of more meetings - the only fix is to make the business more investable in the first place.

2. Make fundraising energizing, not demoralizing.

Many founders dread fundraising because of fear of rejection. Russ’s perspective is refreshing: if you can set aside that stress, fundraising is a rare opportunity to get free feedback from some of the smartest, most positive people in tech. Good VCs show up every day hoping to hear the wild vision that could change the world. You’ll never get this concentration of brainpower anywhere else. Treat fundraising as inspiration instead of a crucible.

3. Humility wins every time.

The strategy of creating FOMO by treating VCs like they’re the lucky ones? Russ says it’s nonsense. The best fundraiser—and founder—pairs deep confidence in themselves with pure humility and appreciation for anyone willing to bet on them. Founders who walk in believing every meeting is a privilege for BOTH parties build real relationships. Investors partner with people they trust, so don’t fake humility—live it.

Russ’s skills are legendary, but behind those skills are the inspirational character attributes of honesty, humility, and relentless focus on improving the reality of the business - not just the story you tell about it. And across dozens of companies and hundreds of rounds, those are the characteristics that I have seen most influential to winning a capital advantage for you and your company. .

For more wisdom from expert founders and fundraisers, hit subscribe here on Substack. And catch Raiser’s Edge on YouTube, Spotify, and Apple Podcasts for more conversations with the people who really know how capital gets raised—and how businesses get built.

Stay sharp,

Ben

Dan Shapiro, founder of Glowforge, Ontela, Sparkbuy, and Robot Turtles, is a true expert in that practice of data-driven iteration and improvement, and it has helped him build a capital advantage over and over again. Dan has raised over $200M for his companies, led successful M&As, and broken multiple crowdfunding records - his crowdfunded raise for Glowforge set a record for the most money raised over a 30-day campaign at the time.

But Dan’s data-driven approach isn’t just aspirational—it’s a blueprint that you too can use for a capital advantage. Here are some of my takeaways from my conversation with Dan on Episode 2 of Raiser’s Edge.

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1. Your personal story is the investment narrative.

Dan doesn’t just list his career milestones; he intentionally frames them for every opportunity so they become evidence of founder-market fit. He doesn’t see his career as a zig-zag for no reason, but as a latticework where every job, company, and passion is positioned for its relevance to the business he’s building.

Investors are always looking for founder-market fit, and Dan proactively connects the dots for them—rather than letting them question why he’s gone from wireless carriers to board games to lasers. His advice: If you don’t craft your narrative, investors will, and it might not work in your favor.

2. Build flexibility into your pitch – and your strategy.

Most advice says, “Sell your vision.” Dan flips that, insisting that the best fundraisers are flexible. Your company is a synthesis of the founder’s North Star, the skills, excitement, and theses of the people around the table, and the goals of the investors that are brought in to fund the company.

That flexibility includes how you pitch. Dan tunes his pitch to show how his vision intersects with his investors’ priorities. The best fundraisers read the room and adjust in real-time.

Think of fundraising as a two-way conversation - you’re selling, but you’re also “buying” insights and alignment. That’s the relational magic that leads to a capital advantage.

3. Test everything—but know when data misleads.

I asked Dan about his Glowforge crowdfunding video that made Kickstarter history – it broke the record for top-raising projects. It wasn’t an accident—it was a result of relentless data testing and objective feedback. Dan ran a company “movie night” to break down successful campaign videos, built elaborate decision trees from the best elements, and even ran Mechanical Turk tests to see what actually landed with potential backers.

But he also knows the trap: not all feedback can be read at face value. Whether from investors who keep you twisting with endless “maybes” or from advisors who only see the world their way, Dan knows real feedback is rare and precious—and harder to get than it looks. Sometimes, you have to “declare there’s no data available” and use your best judgment, rather than getting distracted by noise that may be leading you in the wrong direction.

4. The wall is real, but don’t let it stop you (or bankrupt you).

Dan speaks with the honesty of someone who has been through it all: a protracted fundraise can feel like banging your head against a brick wall.

But what really stood out to me is Dan’s discipline around when to stop. In this episode, Dan tells the story of his first start-up. Before he started raising, he and his spouse agreed on a hard deadline for how much of their runway they’d spend on this pursuit—if it didn’t work, he’d walk away. Founders don’t talk about this enough, and it’s the difference between “one more try” turning into heroism or devastating ruin.

Dan’s approach is a reminder that great fundraising isn’t a mystery—it’s a method. It’s the discipline to test, refine, and recalibrate, paired with the confidence to throw out false signals and trust your judgment when the data runs out. The founders who treat every conversation as insight, every “no” as information, and every pitch as a prototype are the ones who build a true capital advantage - and with the help of Dan’s playbook, you can unlock one too.

Want more wisdom from top fundraisers and founders about how to join their ranks? Subscribe to Raiser’s Edge, on YouTube, Spotify, and Apple Podcasts - every other week I sit down with an expert founder and share new, practical insights on the ways they geared their raises toward success. And if you want to get more strategies, and behind-the-scenes takes like this straight to your inbox, subscribe here on Substack for our bi-weekly emails!

Stay sharp,

Ben

As so many founders know, raising money can be a very rough ride. The highs, lows, and narrow escapes are part of the package.

For our pilot episode of Raiser’s Edge, I talked with Yifan Zhang, Managing Director at the AI2 Incubator and a two-time founder. Yifan revealed what it’s like to navigate fundraising through a truly existential crisis—and her secrets that let her come out the other side.

Yifan’s path—through viral launches, hard pivots, and existential near-death moments—reveals truths about fundraising you just won’t hear anywhere else. Here are my biggest takeaways from our conversation, plus some raw, behind-the-scenes insights that didn’t make the episode.

1. Treat VCs as equals.

Early on, Yifan battled the feeling that VCs are “above” founders. Her breakthrough came from realizing she was an expert in her tiny sliver of the world and investors had just as much to learn from her. The best investors, especially in Silicon Valley, operate as equals. Wherever you’re raising, own your expertise in the room—it’s vital, not just for confidence, but for deal quality.

2. Ignore the happy talk; focus on actions.

Investors may talk excitedly—but it’s their speed to the next action (intro, diligence, term sheet) that proves real interest. Keep tabs on those action gaps and don’t let the “happy talk” lull you into complacency. Instead, track action follow-through and timing between actions.

3. Fundraising is a process—and organization and execution are key.

Yifan runs her raises with the precision of a sprint—batching intros and managing timelines. If you’re raising, try structuring your rounds in mini-sprints, rather than endlessly chasing warm intros. Efficiency and consistency can take weeks or months off your timeline to raise.

4. Disaster can be a catalyst for great fundraising.

When COVID hit, Yifan lost 90% of Loftium’s revenue in four days. Instead of panicking, she hit the chaos head on and used the crisis to organize a better model. Investors don’t give you any credit for adversity—what matters is the trajectory that you emerged with. By focusing squarely on resetting with a smarter business model, Yifan unlocked the next round.

5. Make Sure to Recharge

Yifan described fundraising as “getting punched in the face repeatedly, and just getting back up”—but emphasized the need for breaks and support buddies. Even the best CEOs need space to collapse, process their emotions, and come back at full strength. If you’re in the midst of a brutal raise, don’t go it alone. Be deliberate about having a support crew and allowing for moments to recharge.

Yifan’s journey isn’t just about tactics—it’s about mindset. She treats failure as learning, embraces process over perfection, and sees fundraising as an integral, recurring test of leadership.

The true edge in fundraising? Being ruthlessly honest about what you know, what you don’t, and exactly what you learned in the fire.

If you want to learn more secrets from the best fundraisers, subscribe here on Substack, as well as on Spotify and Apple Music—so you never miss an episode drop.

Stay sharp,

Ben

Fundraising has one of the most extreme skill gaps in startup life. Some founders make it look easy and land monster FOMO rounds in days.

But most founders aren’t in a hype sector and don’t have the magic touch of a Musk. Instead, they slog through hundreds of meetings—often with no term sheet to show for it.

The gap isn’t just about product or market. It’s about mastery. The best fundraisers know how to translate vision into conviction and use investor psychology to their advantage. Their raises don’t just fill a balance sheet—they change a company’s trajectory.

Raising capital is a skill any CEO can master—as long as they have the right resources. That’s why I created Raiser’s Edge, a new podcast, hosted by me, Ben Elowitz. Each episode takes you behind the scenes with top raising founders, uncovering the real, hard-won, actionable secrets that allowed them to gain a capital advantage—so you can, too.

Some tips from this upcoming season of Raiser’s Edge:

1. Design your company to be investable.

In my conversation with David Shim (Read.ai, Placed), he cautioned founders against pitching their startup without proving product–market fit. Most VCs already run their own analytics—they often know exactly where you stand before you’ve even met. David stood out by supercharging PMF so his numbers lit up those screens, and investors started chasing him.

2. A “no” can be just as valuable as a “yes”.

During our pilot episode, Dan Shapiro (Glowforge, Ontela/Photobucket) talks about how he sees rejection from VCs not as failure but as feedback. Each “no” is a chance to refine your pitch—as long as you learn how to tell genuine critiques from polite brush-offs.

3. Investors aren’t buying your product.

In my interview with Gregory Mark (Backflip.ai, Markforged, Aeromotion), Greg put it simply—investors buy companies not products, so it’s not what you make, it’s how you make it. No matter how great the product, your pitch needs to be about the business behind it. Your model, margins, and momentum are what they’re betting on.

The common thread? None of these masters were “born” fundraisers. They learned, iterated, and built the skill that got them capital and outcomes—and you can too.

On Raiser’s Edge, you’ll get these insights and more tools, hacks, and insider advice you can’t get anywhere else.

Ready to learn from the best and level up your fundraising game?

Watch the trailer below! And subscribe to us here on Substack, as well as on Apple Podcasts & Spotify to make sure you don’t miss an episode - our first episode, with guest Dan Shapiro, drops next Tuesday, November 11th.

Let’s raise the bar together.

– Ben