Is It Harder to Raise Money in 2026 Than 5 Years Ago?

0:00 Cold open and welcome

Max: Thanks for tuning in, and welcome to The Funding Table. This is a show where we discuss all things venture capital, startups, and raising money, with the hope that you avoid some of the costliest mistakes that we made. If you're new here, welcome - and if you're returning, it's been a little bit since our last episode. You might recognize some familiar faces, but there are some new ones here as well. Before we get into the main conversation, let's do some quick bios and introductions so you know exactly who you're hearing from.

1:08 Max Goldberg, Mike Spidaliere, Sam Poon, Cam Owen

Max: I'll go first. My name is Max Goldberg. I'm a two-time exited startup founder, Techstars alum, and former investment banker. I'm currently the founder and managing partner of GoldCapital Consulting, where we help early-stage founders raise capital. I'll turn it over to you, Mike - welcome back.

Mike: Appreciate it, good to see you, brother. Multi-time founder myself. I recently started this firm, First Time Founder Capital, where we work with early-stage founders to help them get to the point where they're both investable and investor-ready.

Max: We'll turn it over to the first new face, Sam Poon. Welcome to The Funding Table.

Sam: Thank you so much. Like Max mentioned, my name is Sam Poon, and I was on the venture capital side for many years. I was in the room where the decisions were made before founders actually got funded - and I've been on the other side as well, speaking with family offices and endowments, raising for those venture capital funds.

Max: Awesome, Sam, and welcome. And the final new face, last but not least - Cameron Owen. Welcome.

Cam: Appreciate you guys having me here. I haven't heard my full name used in quite some time, so thanks, Max. I'm Cam, the new face here. I'm a former exited founder - and I bootstrapped the whole way, so no raising experience, similar to probably many of you watching. It's been a blast learning more about it through the years. I've spoken with a lot of early-stage startup founders, and similar to Max, I help you all with the raising side of things.

Max: It's worth establishing the lanes here if you're new. Two of us, Mike and myself, are former exited founders who both raised money before. On Cameron's side, a bootstrapped founder who's talking to founders all day. And of course Sam - the VC, the man from the dark side, in the room. So we have some unique perspectives, and an interesting topic set for today.

First and foremost: why are we doing this show? We want to make sure that startup founders who are thinking about raising money, or actively raising, can avoid some of the mistakes we made on our own journeys. But more so - these are the exact conversations we're having every day with paying clients of ours, at Mike's firm FTFC and at GoldCapital, working with startups on their rounds. A lot of this is gatekept information. Our hope is to open up the conversation and share more of it online for free - with the hope that at some point you become a paying client as well. So without further ado, let's get into it.

3:51 Airtable fire sale: what it means for founders

Max: Michael, we got a juicy headline in the news. There's a company, Bending Spoons. There's Airtable. What the hell is going on, and why is it relevant?

Mike: This acquisition happened about two weeks ago, so all this information is just starting to flow through. Absolutely fascinating. Airtable started in 2012, really became operational in 2013, and raised their Series C through Series F in the peak-ZIRP era during COVID. Their last valuation was $12 billion in 2021 for their Series F - and they just sold for $1.3 billion. A little over $2 billion in total equity value, because they had roughly $960 million in cash sitting in their war chest. That's about an 80% haircut on the peak valuation, for anyone not trying to do public math. A lot of people are seeing this as the AI scaries - is this AI coming in and destroying legacy systems? Did the founders walk away with zero? Did the investors? Is this a lose-lose for every side?

Max: Sam, you spent almost a decade in venture capital. It's still unclear exactly whether the founders walked away with something - they might have taken secondaries on the way up, hopefully. But who came out on top here? Who lost money?

Sam: Great question, and there's so much to unpack with AI, so I'll leave that for later. Who lost money, who made money, and who made out like a bandit? It's interesting Mike mentioned the ZIRP era - let's say that ran until 2021, though 2022 is really when things got frothy. Even the late-stage investors got their money back - what we call the liquidation preference. They got 1x. So they didn't lose money, but there's an opportunity cost: they could have invested in other startups. Who's fine? The early funds did great - Airtable's first round was around 2013, so they got in cheap. The founders, of course, did fine. But who actually lost? I'll just say it: the LPs could have invested in an index fund. The later-stage investors only got their money back, and those returns look abysmal compared against what the public markets are doing. And honestly - the employees. They don't get preferred stock; they get common stock, so they're last in line, and their options were priced against that $11-12 billion. They didn't do too well.

Cam: I'll chime in here. Why then would someone even want to raise? As an early-stage founder - we talk to a lot of pre-seeds and seeds at that stage - why go the VC route if, down the road, you can get this to $12 billion, think about how much time and effort and sweat and tears that takes, only to do a roughly $2 billion exit? Why would you even raise VC at that point?

Mike: That's a really good question. At the end of the day, they would not have gotten to where they are today without VC dollars. They could have grown by profit, but they would be significantly further back without those earlier rounds. Back to Sam's point - I was doing some digging before this pod. Freestyle, Box Group, Caffeinated Capital, even our guy Ashton Kutcher came in and got about a 45x return as the earliest seed investors. At the end of the day, we work with early-stage founders, and a lot of the investors we work with are early-stage too. Even in a scenario with this 80% haircut, the valuations they invested at were significantly lower than the roughly $2 billion final sale price - so they still made out. Very unfortunate for the later stage: you invest $300 million, you get $300 million back, but that capital could have gone into a lot of other avenues and made a significant return. We saw SpaceX IPO in the trillions. This is definitely unused capital for the later-stage investors.

Max: I think there are a couple of lessons here. Assuming you're a founder looking to raise that first round of institutional capital - a pre-seed or a seed - you might go a decade or more on a journey and break your back to make almost nothing. Making even $5, $10, $20, $30 million on a billion-dollar outcome, which is the case in these horrific scenarios, is really bad. You might do better creating a local plumbing or HVAC business if those are the dollars you'd make over a 13-year period. So two things are extremely important. One: you have to understand the concept of a liquidation preference, because that's really the root cause here. Very simply, a liquidation preference means there are folks senior to you in an acquisition - they get paid out first. Your investors always get paid first because they have preferred stock, usually with a 1x liquidation preference. But if companies are in dire times or can't raise, you might hear about 2x or 3x liquidation preferences - absolutely terrible - where investors that come in at the tail end are entitled to double or triple their money before you, the founder who spent your whole life building the thing, see anything. Be careful with liquidation preferences. And two: we see a lot of performative founders in the Bay Area coming out of accelerators - I was in one - who view valuation as a prize. "Hurrah, I got my $20-30 million valuation at the idea stage." That's an obligation. As Mark Cuban says, it's a promise - you have an obligation to your investors. Don't celebrate the valuation; that's just the start.

10:50 Is 2026 really a record year for VC funding?

Max: Moving on. Sam, the headlines are showing that VC funding is breaking just about every record. In the first half of 2026, more capital has been raised than in all of 2025, and something like 41% of all venture dollars this year have gone into literally two or three companies - two of them being OpenAI and Anthropic. So I'm curious: VC is breaking every record, but a lot of the founders who come to work with us are talking about how difficult it is to raise money - maybe the hardest it's ever been. Why is that?

Sam: Max, both things are true at the same time: record funding, and a really tough time to fundraise. There's more money in venture capital than there's ever been - but it's already spoken for. Like you mentioned: two companies, OpenAI and Anthropic - who doesn't know who they are - took 40 to 45, almost 50 percent of every venture dollar on earth. Not just the United States - on earth. And that came out of just three funding rounds. Three. Here's what the record headlines hide: fewer companies got funded than last year, not more. Even at the earliest stages, dollars went up about a third while the number of deals went down. It might be record funding, but it's the same year moving in opposite directions. If you're a founder reading "record funding" and thinking it'll be an easier time - you're reading the dollar amount, not the deal number.

12:48 How do I plan my fundraising strategy in 2026?

Cam: Can I ask you something on that, Sam? From a lot of the founders I speak with every day - it sounds like a lot of the smaller raises get hindered by this, even when they may only need $250-300K. Those are the people not getting funded. These VCs and family offices - their check sizes have gone up; fewer deals, more money in each deal. Does that mean I, as a founder, should be looking for more capital than I thought? Or does that hurt me?

Sam: It absolutely hurts you. VCs stress-test a few things when you pitch them: how much are you raising, where is this going, and what are you going to unlock with it? Raising just for the sake of raising sets your expectations way higher. If you don't meet those milestones, your company might go under - and a VC is thinking you might never meet those metrics; it sets the bar too high. It has to be strategic. A lot of founders don't understand this. Be intentional and have a real plan in place.

Max: The converse is also true, though. Taking on more capital at higher valuations means greater expectations to live up to - maybe on a sub-one-year timeline, the way companies are raising, deploying, and raising again now. But raising less money can be an anti-signal too: maybe the founder isn't ambitious, maybe they don't understand how venture works, the market-share grab that's expected, the grow-or-die nature of it. So Mike - funds are undeniably sitting on more capital than ever, and clearly passing on some really good companies from a fundamentals perspective. How does this macro environment change how much runway you should raise for?

Mike: It's incredibly important to think about. Going back to one of Sam's points - there are more venture dollars out there than ever, but because of AI there are also more companies going out for those dollars than ever, because people can launch over a weekend and see ARR in record time. Whether those companies are fantastic or bad, they're fighting over the same venture dollars you are. There's always this quandary: should I raise as much as possible so I don't have to worry if the market is dry a year from now? But you also don't want to over-lever yourself. You don't want to hit a $40 million valuation pre-product or pre-revenue and then spend a year trying to grow into it - because eventually you're up against people who have spent 15, 20, 50 years pricing rounds, and that's when things get dicey. On runway: VCs are expecting another round in a year or so - if you're scaling really fast, six to eight months, though that's rare. The smartest move is to bake in a bull case: 18 months, even 24. But make sure that if you use that cash over 24 months, you have the metrics and traction to raise the next round. Don't slow-roll it. Keep some working capital in the bank, but if you raise three million, don't sit on two million for a year and a half. As Max loves to say - it's called burn for a reason, baby.

Max: And I'm happy you gave a specific timeline, because a lot of industry content gives wishy-washy answers. As you'll tell from this episode, we're straight talkers - we have opinions, and that doesn't mean they're correct for every company.

18:08 Biggest fundraising myths founders believe

Max: The takeaway is: there's what you communicate to the venture market to raise capital and nurture your cap table - and then there's your internal strategy as a founder, which might be a little different. If everyone's burning cash right away, maybe it makes sense to be contrarian and prepare for a down cycle. That doesn't need to be core to your narrative - you don't want to look like a hoarder, and the last thing you want to hoard is dollars - but be smart, because so many companies are dying right now, and we just talked about a terrible outcome for a company that probably wishes it had more cash on hand. Cam - for those who don't know what you do, you're on the front lines talking to folks who want to work with us. We have a very low acceptance rate and a tremendous number of applicants monthly. You've been telling me how many people come in not knowing how much they should raise. They undershoot - "I want to raise 500K, 750K" - and lately you walk them up to the $2-3 million range in most cases. What's the response when you tell them they should consider raising more? Do they realize that's even possible?

Cam: Great question, and I have been noticing it. I'll put this out there for all of you UK founders: 500K is not the answer. For some reason, every UK-based founder, when I ask how much they're raising, says 500K - every single time. Whenever we get into that discussion, I honestly see the gears start turning. They're thinking: wait a minute - everyone around me kept saying "you're too early, raise a bit less, that's all you need to get to the next rung." But VCs are fundamentally playing the game of "I need you to get five rungs up the ladder as fast as possible, because most people fail, and I need to know if you're a failure or a winner - and if you're a winner, they're going to keep funding you until you get all the way there." Once that's said, they naturally start to grasp it, and it's fun to see. In these pre-seed and seed rounds, it's not crazy to ask for $2 million, guys. It's really not.

Mike: Let me drop a little knowledge here, because I get asked this constantly - "how much should we raise to hit these milestones?" A core issue a lot of first-time founders miss: you price out this round, but you also need to look at what the next round's traction metrics are in the current market. What are investors funding at seed or Series A? Are you actually going to hit those traction metrics with the amount you raise? If you raise 500K - will you be front of the line for that next round? That's what I always tell founders: raise enough to be front of the line for the next round.

Cam: I don't know if these people have ever run advertisements, or have any clue how much marketing spend takes. 500K gets you to about next month. To Mike's point - to hit the metrics you'll need for the next raise, you need more than you're thinking right now, because it takes a lot to get there.

Mike: And you don't want to be the founder who gets ten yards from being first in line - or even accepted by VCs - having burned all your cash. Do you raise a bridge round? Do you grind toward profitability for more traction? It's a tricky spot, and I've seen it happen many times: they simply hadn't raised enough.

Max: That's the key. A lot of folks come in without a clear definition of what the round needs to accomplish - there are going to be two or three KPIs that matter, investors will hold you to them, and frankly you should hold yourself to them. And even sophisticated founders tend to view their growth subjectively, in their own lane. But as we discussed - 40 or 50 cents of every venture dollar is going to two companies that grew from zero to billions in ARR in 18 to 36 months. That's the objective landscape you're being measured against. You can't define success in a vacuum. VC is a zero-sum game: you're not just competing against direct competitors - you're competing against Sam Altman and Dario and some of these cannibals. They're very good at raising money. They sold everyone on the idea that we're all going to be replaced and have no jobs - that's clearly not occurring, or at least not yet, but it was a really good fundraising strategy.

24:05 What salary should I take while fundraising?

Max: There's a formulaic way to think about how much to raise - and I don't like distilling things to formulas; our engagements are custom to each founder and startup. But really, the formula is: cash needed to get to the next milestones - the cost of getting there - plus a buffer, that margin of error, sized to what VCs expect for companies in your space. You can compute the absolute cost, but then it sits on a curve against what other companies are raising.

Mike: I want to ask Sam a question, because I've seen this a handful of times recently and it's amusing. Sam - a company comes to you back in your VC days raising $2 million, and in their financials you see that as soon as the raise closes, the CEO pays themselves 500K. What do you say?

Sam: There is an expectation - a range - at pre-seed, seed, Series A and beyond for what a founder, a co-founder, an engineer should be paid. In venture capital, when we hear a pitch and see misalignment, we start to think: maybe the incentives aren't there. Maybe they think it's all glamour, a cushy job. Are you ready to grind through the pain? Are you actually in this? Would you still be building this company if you never raised a dollar of venture capital? Sometimes it's "I want my lifestyle to change" - that happens eventually, if you're successful and in it for the right reasons. Not everyone needs to eat ramen noodles every day - nothing against ramen noodles - but...

Max: But Sam - I was a management consultant at McKinsey for two years. How do you expect me to live off less than $250,000 a year? I live in the Bay Area.

Sam: Funny you mention the Bay Area, because we're in Boston and it's not cheap here either. Management consulting pays well and the hours are long - but in startup world, the hours might be even longer. You're wearing many hats: talking to customers, VCs, suppliers, working your supply chain. You have to be in it for the right reasons. As a venture capitalist you check the market, what they're building, the macro - but it's also a gut check on the founder. Is the passion there? Do you have domain expertise? Are you in it for the right reasons?

27:08 Why is fundraising so hard right now?

Max: Well said. I want to transition, but before we do - Sam, honest answer. Is it easier or harder to raise money as a founder now than it was five years ago?

Sam: I'm going to say it is way harder now to raise money than it was five years ago. And I'm going to stick with that.

Mike: I'm in the same boat. Like I said earlier: more venture dollars than ever, but more companies coming out fighting for those dollars.

Max: Tell me about that competition. What does that mean?

Mike: Look at some of these industries - say, AI scribes for healthcare. A year and a half, two years ago, that was a brand-new idea. About 30 days later there were 60 companies in the market competing for those venture dollars. It's specific to your industry - is what you're building extremely novel, or does it only have one or two competitors? But people are spinning up companies every single day. It has never been easier to start a company, and with all the content out there, everyone thinks they should be on the venture route. You're competing against every single person trying to build a company and get on that flywheel.

Cam: I'm going to take the direct opposite approach. To your point, Mike, more people than ever are raising and building - and guess what, a lot of them shouldn't be building their businesses. When you're a true startup founder who understands where you're going and has domain expertise - and let's be real, you can build anything quickly nowadays, so you can reach the scale you need to raise serious dollars - this is a game of distribution. If you can nail distribution, it has never been easier to stand out and raise a real sum from venture capital, family offices, or the like. More competition makes the stars shine brighter.

Max: I'll give my take: I think it's way easier to raise venture capital now than five years ago. It's way more competitive - but if you're genuinely a killer and understand that you have maximum leverage and there are zero barriers to entry anymore, you can seize the opportunity. When I was putting together a small friends-and-family round in 2021 as a college sophomore and went online to learn how to raise, literally all that existed was YC Startup School - which is phenomenal, and still is - and that was it. On Instagram, TikTok, YouTube, there was almost nothing in between. That's the gap we're selfishly trying to fill. But there's so much more leverage now: a thousand more startup accelerators, and pretty much every major American college - and some European ones - has a program devoted to giving you your first check. Distribution is free, product development is free. Our grandparents built businesses in manufacturing and textiles, where you needed incredible access to capital just to start. Now you can prove something out easily - but you have to go the extra mile to stand out. Having $50,000 of your uncle's money to build an app isn't the advantage it used to be. It's truly a skill issue now.

31:56 Should I call my startup an AI company?

Max: Cam, you recently told me a story worth bringing up. Someone applied to work with GoldCapital and FTFC and ended up becoming a client - we'll keep the details anonymous. Experienced founder, operator, worked in corporate turnarounds, and he's wondering: "How much should I be leaning into AI as a founder?" They weren't an AI-native business, but they felt silly not mentioning it. How do you navigate that?

Cam: Great question. The biggest issue they ran into is finding investors that aren't just AI-crazy - we were discussing the other day the forward-looking multiples AI companies are getting; how can you not want to claim AI in what you're building? But there's a fine line in deciding how you use it, how you scale with it, what part of you it is. A lot of founders are seeing this and thinking: "I'm not really an AI company, but do I BS my way through and tell an investor I'm very much leveraging AI - and then just sound like everybody else?" Sam, as the VC: what do you think of people who claim they're an AI company when at the core they're not? Advantageous - or have you seen so many fail that you'd rather the raw, authentic look?

Sam: We've seen the shift in the market, and a lot of founders don't realize it. Five years ago it was all about growth; then it became profitability; nowadays, in the AI era, it's a mixture of growth and defensibility. Here's the thing. If you claim you're an AI company, the first thing an investor looks at is your margins. If you call yourself AI and your gross margins look like a services business, a VC thinks: you must be paying humans somewhere in that loop, and you just didn't mention it. We're going to sniff that out and stress-test it. And retention - AI gets people to try your product, but the real product is what keeps them. One question I'd ask: what happens if Anthropic, OpenAI, or a frontier lab ships this exact feature next month? If your answer is "we might lose in this space" - that's not a company. It's a head start, and it's a feature.

Max: Silicon Valley has been dominated by the fake-it-till-you-make-it mentality forever, and it's gotten plenty of folks in trouble - including, recently, a very wealthy gentleman's daughter. It's hard to imagine building a LinkedIn or Airbnb without some viral or almost artificially forged mechanism to get people on the platform. Gaming companies have done it for years - multiplayer mode where you're actually playing against a bot in the early days. It's branded as "do things that don't scale," which can help a company - but you can also cross the line. We heard a story from a client about a startup doing "AI checkouts" - a service that helps you check out online, marketed as an AI-native platform - and it turns out they had a hundred people in a click farm doing the checkouts manually. Zero AI, no agentic use case, nothing - and the founder gets charged with fraud. Feel free to fact-check the story, but we've heard stuff like this. So in due diligence, beyond the margins - what's a telltale sign something like that is going on? And Mike - when you're talking with clients, how much can you lean into these fake-it-till-you-make-it opportunities that are so tempting with agents? Is that a viable strategy?

36:50 What do VCs check in due diligence and data rooms?

Sam: It's an absolute doozy. Founders typically pitch what they built - they're selling, hiring, and shipping all day; that's the founder muscle. But that's a customer pitch. What VCs do internally - the investment committee - is a completely different exercise. Those calls are three hours. We're in the data room, stress-testing your customers and your product. Even "frictionless checkout" was a thing for a while - startups tried it, big incumbents tried it, and it turned out it wasn't frictionless at all; there were people verifying receipts at the end of the day. We're constantly on customer calls. We look at the market, where things can go wrong - and where they actually will go wrong. We look at the business model, whether it expands the competitive landscape, and - Cam mentioned this - your distribution. What can go right and what can go wrong, super intentionally. During boom cycles, most firms go a little light on diligence - but that's not how I was taught. You might have the best product and be the right people - but does your story hold up? Answer these questions internally before you ever speak with an investor. You can't go in hoping for the best.

Mike: I have a strong preference on this. Look - I said hi to Claude this morning. That doesn't make FTFC an AI-native company. If you're not actually an AI company, own it - and flip the conversation: "While we're not currently AI-native, that doesn't mean we won't be. Here's how we're using AI internally today, on the team side and the operations side. We're not building the next chatbot, but we're leveraging AI in a way that makes us 10x more effective." If you lie about it and an investor opens the data room and sees no AI infrastructure in your product folder, their first question is: where is it? Are you going to keep up the facade? Why not just go with the honest truth and focus on finding investors open to these types of companies? Every investor is investing in AI - but plenty are still investing in companies that leverage AI without being AI-native.

Cam: Take the stark stance. Elon saying he'll build rockets doesn't mean much - Elon saying he'll colonize Mars does. Say: "Yes, we're not a completely AI-based company - here's why." And if you don't have a good why, become the AI company: if there's a reason you should be using AI, implement it, then go raise on it. But same as the other two - never claim and put up a facade that you're an AI company just to raise capital. Never.

Max: Mike mentioned one word specifically - data room - and that might be unfamiliar to some. When I posted about this on Instagram months ago - founders, you need your data room ready - I got a host of comments from know-it-alls who've never raised money saying "you don't need a data room." Sam has probably reviewed thousands of data rooms as a VC; Mike has worked through easily one to three hundred over the last few years. A data room is an essential deliverable of your fundraise. It's the boring, bureaucratic process of assembling legal documents, tax IDs, incorporation documents, repositories - but the detailed write-ups are strategy, especially in how VCs actually consume the diligence materials. And now, with AI - I just got off the phone, and this is the first time I'm dropping this on the podcast, free game if you're listening. My buddy from Techstars got into Y Combinator with his next company and is building a large AI defense-tech company - he'd be mad if I gave exact metrics, but call it close to $10 million ARR as of last quarter, backed by Paul Graham, Pear, CRV, and other amazing investors. They went out to raise their Series A a week ago. He told me, laughing: "Max, we sent the data room and the financial model" - and by the way, nobody had even asked for a model at seed. Then the leaders at major funds started passing, saying the financial health of the company wasn't strong enough. When the founders ran the model through their own Claude window, they got the same response: this company is weak. First lesson: VCs can be incredibly lazy - some are dropping your data room into Claude and passing or proceeding based on what it says. We have clients who do that with our agreements too - you probably want to use your brain. But here's what they did: they added small footnotes to the bottom of the Excel workbook contextualizing the numbers - explaining that part of the revenue was contracted, part was design revenue. And suddenly that same Claude instance is saying "invest immediately," and their conversations are progressing. A small change, guiding the AI you know will be reviewing your materials - free game for anyone listening. And if you get this kind of value from these conversations, imagine what you get as a client, because we won't go into 95% of what we know here. Cam - to wrap this thread: a founder comes in asking how much to lean into AI. What are you telling them?

Cam: The general take is what we've discussed: don't over-leverage it - it will hurt you. In the last year alone, enough investors have fallen for it that they've put their guard up. They'll do exactly what Sam said - the sniff test. Going in saying "we're an AI-native company" when you're definitely not: don't. You'll get to diligence, maybe slightly past that conversation, and you'll get blocked. Be truthful. If there's a reason you should have AI, implement it. If not, own it and explain why it doesn't make sense for your business.

Max: And if you're confused, or your current positioning isn't working - shameless plug - click the link in the description and apply on our website. If it makes sense, we'll book a completely free call to go over your situation. These are exactly the problems we tackle - and even where we don't know, we can go test in the market, get you in front of investors, and learn quickly what the positioning needs to be.

45:41 Should I give a VC a board seat?

Max: Moving toward wrapping up - the most viral conversation going on right now, certainly on X - or Twitter; I still call it both - it's making its way into every founder group chat: the Travis Kalanick announcement interview. If you don't know, TK was the founder of Uber - a legendary founder with a real temper, it sounds like, but no doubt a legend behind one of the biggest companies ever created. It turns out that for the past five or six years he's been in stealth, with employees under ruthlessly strict NDAs, building physical AI - a company called Adams. In this podcast interview, his hot take, paraphrasing: maybe 1% of VCs are actually helpful and provide value, and the rest are either a complete distraction or outright destroy value. Sam - you were an employee at a fund as of a quarter ago. Are VCs helpful or not?

Sam: I'll start by saying I call it Twitter - because when we say "why are we talking about my ex?"... But here's the thing about Travis Kalanick: a former general partner I worked with - great guy, smart, down-to-earth like most VCs in my network - worked directly with Travis and was an early investor in Uber. Travis has a lot of hot takes. I'll say this: the best VCs go into a call with a founder expecting to learn something. What VCs have seen are the ebbs and flows - downturns, hot markets. That said, most VCs trip themselves up thinking "I need to be on a call every week, I need to set direction." Sometimes they get in the way of the founder, when it should really be about writing the check and opening up partnerships. Quarterly calls: "How's the company doing? Anything we can do? Because we've seen this, we know these people." Some VCs get in the weeds a little too much.

Mike: There needs to be a fundamental match between the founder and the VC. From what I've seen of TK, I can't imagine he's one for daily standups with his investors. With his network, knowledge, and capabilities, he's not looking for the hands-on, down-in-the-dirt value-add investor - whereas someone who's never done this before benefits from that significantly. The founder needs to understand what type of investor they want. Do they want the handholding? Or do they want to take the cash and report back in a year when they're raising again? I've seen investors provide significant value when the founder wants it - and I've seen investors destroy it.

Max: One thing I want to call out, because it's sensitive: the DOJ - for international folks, the US Department of Justice - is actually probing Andreessen Horowitz right now over board seats. Two of a16z's portfolio companies, Databricks and Fiverr, became competitors, and there's an antiquated 1914 antitrust statute, almost never applied to VCs, that's now being used to look at what board members can disclose to management at their portfolio companies. If you're pitting two of your portfolio companies against each other - that's what's alleged, at least, and being investigated. Does this make top firms board-shy? Do you want investors on your board with enormous portfolios who have a lot to lose? What does it mean for founders who give up board seats when they raise larger amounts? Sam, your take.

Sam: I didn't expect that question - everything ties together, and I can talk about venture capital all day. I could get into the history of Dodd-Frank and its exclusions for venture capital - I see the smiles already. For founders: be optimistic and excited. If you're not one of the companies raising these mega-rounds, there will be more opportunity from emerging managers. What's the statistic - something like three-quarters of all dollars raised went to the mega-funds? Those funds can take the hit when they get it wrong. They're great investors, but the emerging managers have a chip on their shoulder, and they're the ones investing in companies with great ideas. The established investors behind mega-rounds will keep taking board seats - they're more inclined to. But as a founder, see this as an opportunity. And here's the thing founders don't realize: venture funds have a clock. 2022 was probably the last really hot year before the downturn, funds typically run a five-year deployment cycle, and we're almost in 2027. There's a timeline pressure to deploy this capital. I think there are going to be way more opportunities right now for founders to get funded - especially by emerging managers who see something that isn't following the trend.

52:36 Fundraising advice from GoldCapital Consulting

Max: That's a nice way to set up our close - stick around for it. Let's say you're a non-frontier founder. You're not a former OpenAI employee, you're not a member of Anthropic's technical staff - which turns out to be probably the most Avengers-like roster of technical talent, former founders of billion-dollar companies working as individual contributors, obviously looking to cash in on that IPO that's coming. You're a normal founder - main street, like how we all started - gearing up for a seed round in the next 90 days. From everything discussed on this show: one thing you're going to do, or do differently, to be successful. Tight answers. Mike, you first.

Mike: Can I start with a what-I-wouldn't-do? Don't wait until you have 30 days of cash left. I have had this conversation too many times. It is very unlikely you'll raise a round in 30 days unless you're incredibly hot. Don't put yourself in a position where, if you can't do this very difficult thing, your company is under. It does happen - but it's not what happens most frequently. What I would do is two things. Everyone can build companies these days; not everyone can build traction in a quick and significant way. Every single investor is looking for the traction story - how you got it, whether it's sustainable and scalable. Traction, traction, traction. It's incredibly difficult to raise pre-traction these days. And second: find the right investors. Not every company is a fit for a16z or Sequoia or the brand names founders want on their cap table. Emerging managers - fund one, fund two, fund three - can bring immense value and are looking for exactly your type of company. Do the digging most founders don't do: who's the best fit, whose portfolio could you partner with or leverage as customers? Understand your ideal investor profile, build the list, and go.

Max: So: don't come into a raise thinking 30 days is enough - even though we've had clients raise on extremely fast timelines, that happens with help. Bake in a good 60 to 90 days of solid fundraising, because there's prep work - materials ready, intros aligned - before you take the first call. There's a lead time; you don't engage a firm like ours and talk to investors tomorrow. And if someone out there is selling you that, it's either cold outreach or they're scumbags, fakers, and thieves - and I'm putting out some videos about the fakers and thieves in our industry, because I'm getting sick and tired of them. So: focus on distribution, get serious about the right investor archetypes and fund names, and figure out how to get networked to them - because that's part of the test. If you can't figure out a way to network to an investor, how will you recruit top talent, sell enterprise logos, win millions of users? There are shortcuts - and if we can be that shortcut for you, you know where the link is - but the test still exists regardless. Sam: one do, one don't.

Sam: The don't: don't build the round just to complete the round - echoing Mike on finding the right investors. The do - come talk to me. That's why I do this: in venture we're meeting companies and doing the research short of making the decision, but I wanted to get closer to the work with founders - founders who are outstanding, building something amazing, but don't have their narrative right and aren't aligned with how investors think. That's a cop-out answer, but I could talk about this all day. And a real don't: don't raise money just because you think you'll reach some arbitrary revenue milestone. Think through who you're targeting, how that changes in six, twelve, eighteen months, three to five years. Be intentional and deliberate. Don't do it because it seems glamorous.

Max: So don't build your company for VCs exclusively - build a real, enduring business and let it stand for itself. And seek advice from people who've done it: the founder's seat and the insider who's been in the rooms making the countless rejections. Have an honest accounting of where you need to be - ambitious relative to your peers, but honest about what you can achieve, because raising a round and then missing the metrics you promised very likely finishes the company. Cam - you're on the front lines daily, diagnosing like a doctor. Number one thing founders should not do to get a seed round done in 90 days, and how do you turn it around?

Cam: The number one thing - true for literally anything in life - is not preparing. Thinking you can throw it together like cramming the night before a test: "I'm sure I'll find some people to give me a couple million dollars, easy." Not preparing is the worst thing you can do - along with not being introspective enough to say: "I've never raised capital before; maybe I don't know what I'm doing and should figure it out." Work with us - or don't; you can do it yourself, it'll just take a lot more time. But put in the time and map it out so you're not doing this the night before investor meetings, or - to Mike's point - the day before you run out of money. And the do, a bit more free value, a conversation I have every single day: figure out your why-you and your why-now. This is sales on steroids - millions of dollars from an investor into your business. Don't just describe your company. "I'm an AI scribe" - fine, I know what an AI scribe does. Why are YOU the exceptional founder who'll make the pivots and turn this into the large-scale beast it needs to be for an investor to see the expected outcome? And why is now the uniquely right time? Figure out those two things. That's sales in every industry - and this is sales on steroids.

Max: Timing is everything, and that story is what raises capital and wins customers. You can't win with a half-assed approach - you're either all in or fully out. From the conversations with founders and clients - we hear constant praise, and forget outcomes for a second: they tell us we fundamentally changed how they view their business and being an entrepreneur. We have dads, moms, college kids, high-school dropouts - clients from the US, Canada, Australia, New Zealand. Massive cultural differences, but after the process they all have urgency. They move with maximum speed and understand the need to be default-alive. Some people come in thinking this is a passive engagement and aren't willing to make the investment - not realizing the help is what makes you move quickly. It's not just the unknowns or the relationships: do you have anyone in your life who actually holds a fire under you? For most people the honest answer is no - zero accountability. Everyone tells them "yes, you're great" instead of "no - this sucks and it needs to get better." If you want that kind of help, you have to seek it out. My answer to the 90-day question: you need one of two things. Either pedigree - some seal of approval from the industry - or you need to be prepared to work a thousand times harder than everyone else. It's unfortunately how the world works: a Stanford CS grad or a Harvard dropout will always have an easier time raising, partly on merit, but mostly because those societal seals of approval and alumni networks run capital markets. For me, coming from a public school - Indiana - the workshop program made us recruit for banking months earlier than everyone else, without the special application links target schools get. You just work harder. When I left banking to raise, I knew I needed an accelerator - a Techstars, a YC, one of those programs - some logo to leverage, because we knew the game and we didn't make the rules. For a lot of founders today, we are that logo. We're not investors like YC or Techstars, but we can be the catalyst - our brand to leverage, our network to leverage. You won't have to create those relationships, though you'll certainly have to nurture them. And if you've been denied from YC 17 times like plenty of people I've heard from - you probably can't just do it on your own. You can bootstrap to metrics and raise later; that works. But you'll pay for the knowledge and relationships one way or another - stock, cash, or opportunity cost. An accelerator takes 7% for information we can teach in four weeks instead of sixteen. Work with someone like us and there are upfront costs, because no one in our position works for free - and anyone who does has no idea what they're doing. Either way, there will be an investment required. Sorry, not sorry.

Cam: Are you saying that someone who doesn't understand risk shouldn't be speaking to investors about the risk of putting millions of dollars into their business? Kind of contradictory, right?

Max: That's the irony. We've talked to thousands of founders and worked with a small couple dozen - very small batch. Some who come to us are wild: "I want $50 million" - on a napkin idea - and the thought of ever investing in themselves in this process is unimaginable. You're going to ask investors for millions with no guarantee of a return, but you have a problem taking the same deal yourself? Figure out whether you're a risk-taker - whether you're an entrepreneur. It's okay if you're not; jobs are good for a lot of people. But don't be complacent: either commit to raising and don't stop until it's done - cutting your losses if it truly isn't working - or commit to bootstrapping. Bootstrapping is awesome; we haven't raised for our own advisory businesses, and it's been fantastic. Both paths are viable. Choose your journey.

Mike: Can I add one last thing? If you're an early-stage founder: don't pick a valuation and refuse to move from it. I've seen companies with strong businesses go under because they wouldn't budge on valuation - and investors understand the market better than founders do in these situations.

Max: I'm so happy you mentioned that, Mike, because we're running long - and next Friday at 12 PM Eastern, that's exactly what we're covering. Probably the most common question we get from clients and prospective clients: how big should my round be? The real numbers on round sizes, valuations, how much to dilute - and what it actually means when investors keep telling you "you're too early." We'd love for you to become a client - there are free resources in the description, our socials, and a link to apply to GoldCapital Consulting. This isn't a course, this isn't info-product junk - it's literally our time, the four of us, working with you from day zero to the end of your raise. And that's the guarantee we offer: we work with you until the round is done. Anything else before we sign off, gentlemen?

Mike: Good to see you guys.

Sam: Looking forward to the next one.

Cam: Crush it.

Max: We'll talk soon. Thanks, team.