A Guide to Raising Money as an Endurance Brand

What I would tell you if you sat down across from me with a deck.

If you are an endurance or outdoor founder thinking about raising money, this is for you. It is what I would tell you if you sat down across from me with a deck and asked where to start. It pulls from the last six months of Long Run Labs conversations, the deals coming into my own inbox, and the founders and investors I have spent the most time learning from.

Before you read

This is written for founders building in endurance and outdoor specifically. The category has its own math, its own customer behavior, and its own capital landscape. If you are building enterprise SaaS, climate hardware, or anything outside this space, the frames here will partially translate but the specifics will not.

If you are building a running brand, a coaching platform, a piece of endurance tech, a recovery product, or anything else aimed at the runner, climber, hiker, or cyclist who actually shows up for it, keep reading.

Quick disclosure before we start: this essay names companies and funds I have financial relationships with, including as an investor and as an advisor. It is my personal commentary, not investment, legal, or financial advice, and it is not an offer or solicitation of any kind. It is written for founders, not prospective investors. Full disclosures at the bottom.

The TL;DR

• The endurance category is in a once-in-a-generation growth moment. Capital is flowing in. Most of it is the wrong shape for most of the companies it is chasing.

• Before you ask how much to raise, figure out which of the seven categories of endurance business you are in. Apparel raises differently than software. Events raise differently than media. The mistake most founders make is treating the whole space as one fundraising market.

• The cost of raising before you fully believe in the business is dilution at a price that reflects the version of you sitting in the meeting, not the version of you who has spent ten years building the thing.

• The investors who matter most for most founders in this category are operator-investors with small checks and large networks, not institutional funds with large checks and limited time.

• The companies that win in this category are elephants, not unicorns.* They own their distribution because the founder built community before product. The moat is the relationship between the founder and the audience, and that relationship cannot be bought, only built. In the age of AI, it is the only moat that cannot be copied.

The rest of this is the long version. Emphasis on long. You may want to read this in the Substack app or online; it will get cut off via email.

Why this conversation is happening at all

Running is in the middle of a rare moment. Strava participation curves are still climbing post-pandemic. Run clubs have become the third places of a generation that has aged out of bars. Trail and ultra have gone from niche subculture to global series. The shoe category has produced more new credible brands in the last five years than the prior fifteen. Norda, Nnormal, Speedland, Mount to Coast. KUIU sold for $800M. Strava acquired Runna. VF owns The North Face, Altra, and several others. Consolidation is happening at the top of the market while the bottom keeps generating new founders every quarter.

Per the State of Trail Running Report, 66% of U.S. trail runners earn more than $100K a year, 25% earn more than $200K, and 7% earn more than $300K. Recently, I spent a week in Tahoe, across Broken Arrow, TrailCon, and Western States. The numbers presented there held up the story. Per the SFIA’s 2025 Topline Report, trail running grew at an 8% annual rate over the five years through 2024, against roughly 0.5% for running overall. There were 16.1 million U.S. trail runners in 2024, up 1.3 million in a single year. The sport is not just adding people, it is keeping them, and the ones it keeps are racing more often. Acquisition plus retention plus rising frequency is the signature of a category that compounds, not one having a momentary spike. I wrote more about this flywheel recently.

The customer is real. The category is real. The result is a wave of capital looking for somewhere to go and not yet sophisticated about where in the map the money belongs. My inbox right now is mostly apparel pitches and tech plays trying to capitalize on the growth, and most of them are pitching the wrong investors.

That is the moment you are raising into. The opportunity is real, but so is the mismatch.

Which category are you actually in?

Seth LaReau writes Trail Waves, one of the sharpest newsletters on the business of trail running. The most useful frame he gave me is the map. The trail running economy breaks into seven categories: apparel, footwear, nutrition, events, media, coaching, and technology. Each category has a different shape. Each shape attracts different capital. Treating the whole space as one investment thesis is the mistake most outside capital is making right now.

Technology and software is the holy grail. Highest stickiness, highest differentiation, compounding revenue, the kind of category where the math actually supports a venture return. Race timing platforms with data moats. AI tools that get smarter every event they process. Coaching software with retention curves that look like SaaS. That is where venture money is not just viable, it is often the right answer. And the mismatch runs both directions. If you are building software in this category and you are trying to bootstrap it out of principle, you may be making the same category error as the apparel founder taking a Series A, just pointed the other way. Some businesses need the capital to work at all.

Apparel and footwear are different animals. Lower margins, inventory cycles, customers who come back twice a year, brand-building timelines measured in decades rather than quarters. The category is real. The math just does not produce venture-scale outcomes for most of the businesses inside it.

The opportunity is barbell-shaped. There is real money to be made in the high-margin, high-differentiation tech and software end. There is real money to be made in the high-trust, patient-built apparel and brand end. The dangerous middle is the founder who tries to leverage the wrong capital structure onto the wrong category. That is where most of the bad outcomes come from.

The first question is not how much to raise. The first question is which category you are in, and what shape of capital that category supports.

Should you raise at all?

The honest answer is sometimes no.

Cole Zucker built Kila Running, an insole company with roughly fifty of the best ultra runners in the world racing in its product, without raising a dime. Tom Evans won UTMB in them. Doug Waters founded Terlingua Threads, a hot weather apparel brand made in Portugal, the same way. Both founders considered venture seriously. Both passed.

Cole came at it from the math. His framing: venture returns depend on a small number of portfolio companies producing something like a 50x outcome, and most authentic brands in this space are never going to be one of them. Which means a fund writing a check into one of those brands is underwriting a different company than the one the founder set out to build. Cole’s argument, and I have watched it play out more than once, is that the pressure to grow into that math is what breaks most of the brands you and I love.

Doug came at it from the inside. He worked on the VC side before he started Terlingua Threads. He saw what venture does to a company when the alignment between the founder and the fund is off. He decided he did not want to build that company. The fund needs a specific outcome on a specific timeline. The founder may want a different outcome on a different timeline. If those two things are not the same thing on day one, they will not become the same thing in year three. The misalignment compounds.

Worth being fair to the fund side here, because the mismatch is not anyone behaving badly. A fund has obligations of its own. The money is not the partner’s, it belongs to LPs with their own timelines and their own people to answer to, and the return profile is a structural requirement rather than a preference. A partner who writes a check into a company that cannot clear that bar has not been generous, they have made a bad allocation with someone else’s money. The misalignment costs the fund too. Which is why the good ones are disciplined about what they pass on, and why a pass is often the most useful thing a founder gets all year.

The mechanics behind that, briefly, because most founders never see them. A fund raises money from LPs and typically has about ten years to return it. Returns are concentrated: a small number of investments produce nearly all of the gains, and the rest return little or nothing. So each check has to be underwritten as though it could be one of the few that carries the fund, because the partner cannot know in advance which one it will be. That is the arithmetic behind the number Cole quoted. It is not a preference, and it is why a fund cannot get excited about a business that will reliably be worth $50M in a decade, even though that is a genuinely good outcome for the founder. The fund owns a slice of that, not the whole thing, so a $50M exit might return a few million against a fund that needs to return all of itself several times over. Good outcome, wrong shape. This is standard fund structure and any VC reading will confirm it.

A third version of this ran on the show recently. Monica DeVreese has been building rabbit for ten years, self-funded apart from three early angels (disclosure: rabbit is a consulting client of mine), while running a retail shop with her husband. Not a decision to avoid venture so much as a decade of proof that the other path works. I wrote that conversation up here.

There is also a third door that almost nobody in this category talks about, which is debt. Not venture debt. Institutional lines from credit unions and CDFIs, inventory financing, revenue-based facilities. For a brand with real orders and unit economics that work, a credit line can solve the same problem an equity round would solve, and you keep the company. A VC friend made this point when he read this, and he is right that for a lot of businesses in this space it is just as smart a play as an angel check. It does not put a clock on you. Worth an afternoon of research before you assume equity is the only shape capital comes in.

If you are reading this and you are not actually sure why you are raising, that is the question to answer before the question of how much.

What does raising actually feel like?

Most founders are not Cole or Doug. Most founders raise something. The question becomes what kind, from whom, and at what cost.

Kyle Siegel founded Raide. $20K on day one with two press placements and no ad spend. He refuses to discount, and word of mouth is his number one acquisition channel. He also made a mistake raising: he took money at too low a valuation because he could not yet see the company Raide was going to become. The investors got a great deal. Kyle paid for it in dilution he cannot undo. His line: if you are not the one believing your business can be big, do not start it.

Ryan Hurley founded Lagoon, a sleep and fitness brand built around personalized pillows for athletes. He raised from friends and family. He lost some of their money in the first year. He went months without paying himself. He spent time trying to sell to everyone before realizing the wedge was specific: position as the pillow for runners, find the niche, win it before expanding. He has been honest publicly about the line between perseverance and stupidity, and about the cost of starting a business when you do not yet know what you do not know.

Kyle’s lesson is about confidence and dilution: raise before you believe, and you price the company at the version of you in the room, not the one who spent ten years building it. Ryan’s lesson is about the human cost. Friends-and-family rounds are not free capital. They are a debt to people who love you, and that debt feels different than institutional debt when the first year goes sideways.

There is a mirror image of Kyle’s mistake, and right now it is the more common one. Taking too much. A round bigger than the business can absorb sets a bar the company then has to clear, and clearing it sets a higher one after that. Founders take the number because it is offered and because it feels like validation. Then they spend three years growing into a valuation that was never a description of the business, only of the moment they raised in. Meanwhile a company doing $2-10M a year with real margins and no board is a genuinely good life, and nobody writes posts about it. But if you can achieve that… congrats, you’ve won!

For those that do end up raising, it often ends up being a cycle that does not stop. You finish one round and you are already onto the next. I have seen this time and time again, and it eats an enormous amount of founder time.

If you are about to raise, sit with both lessons before the meeting. Defend the valuation that reflects the business you actually intend to build. Take the money from people you can stand to face if the first year is rough.

One more voice worth noting on this. Ross Mackay has done the consumer build twice, with Daring Foods and now Cadence, with investors like Naomi Osaka and Stephen Bartlett on the cap table. The line from his episode I keep returning to is about discipline around saying no. Each no costs something in the short term and preserves something in the long term. The founder building their second company knows the difference. The founder building their first one usually does not. The shortcut is to act like a second-time founder on your first raise. Say no more than feels comfortable. Capital is downstream of clarity. The single most useful framing I have collected on the show came from Randi Zuckerberg. She has been investing in this space longer than most of the people pitching her now have been paying attention to it. She built the Facebook Live feature, and has some very well-informed opinions on tech, Silicon Valley, and investing. In the outdoor space, she was an early angel in Runna, the AI coaching app Strava acquired. She has invested in Laurel (disclosure: I am an investor and advisor).

When I asked her how she actually evaluates an opportunity, she did not talk about TAM, CAC payback, or the deck. She said this: “I never invest in a company. I only invest in an entrepreneur. Because every company I have ever invested in has changed from what they originally pitched me.”

The pitch is a snapshot, and the operator is the focus.

Salomon Aiach gave me the operational version of the same idea. Salomon runs his own fund. Twenty-two portfolio companies. He came to running late, ran a 5:17 New York City Marathon and came back the next year and ran a 3:59. He talks about designing for obsession rather than designing for reach. In startups, he said, aim for a hundred super-fans before a thousand casuals. Let your why do the heavy lifting. When purpose is clear, energy shows up.

Megan Lightcap runs the creator fund at Slow Ventures. She invests at the earliest stage there is, sometimes a founder and a pitch deck and nothing else, and the first principle she organizes around is blunt: people matter, brands don’t. We are in the era of the individual. The thing you are betting on is the person at the helm, not the logo, because the person is what survives every pivot the company makes between the pitch and whatever it eventually becomes. It is the same idea Randi named, said from an institutional seat instead of an angel’s.

The second thing Megan said reframes how you should think about your own audience before you ever walk into a raise. Short the mass market. Eyeballs are not worth much anymore. Followers are low signal. The cost of making content has gone to zero, so reach is cheap and reach is noise. What is expensive, and what actually predicts an outcome, is depth: the person who buys the product, knows the founder’s story, shows up to the event, brings a friend. Bigger is not better; a hundred people who would follow you anywhere is a stronger signal than a hundred thousand who clicked once and forgot you.

Randi, Salomon, and Megan are describing one bet from three angles: back an operator with conviction, building for an audience that genuinely cares, clear enough on their why to survive the years between the pitch and whatever the company becomes.

While the deck is the ticket and the price of admission, the conversation is about you, your discipline, your audience, and whether the company you are building is one that compounds the right way over the kind of timelines that actually produce great outcomes. So when you walk into the room, the number to bring is not your follower count. It is your evidence of obsession.

What kind of investor should you take?

The most important shift happening in this space is the rise of the operator-investor: the person who writes a small check, brings a large network, and opens doors the founder could not open alone.

The archetype is someone like Eric Hinman, co-founder of MASA Chips and an angel in a long list of endurance and consumer brands. What makes him effective is not the size of his check. He brings a syndicate of other angels who write alongside him, and he gets embedded in the businesses he backs, distributing, evangelizing, and pulling in his network on behalf of the founders he believes in. The capital is the smallest part of what he adds.

That is the model I try to run my own version of. My checks are small; what I offer is the audience, the network, and the willingness to work. When Hytro came into my inbox through a referral, I signed on as an advisor (disclosure: I hold an advisor option grant) because I could be more useful to them than my check size suggests.

If you are a founder raising in this space, the operator-investors belong in your first round of meetings, before the institutional money. The check is smaller, but the alignment is higher and the help is more relevant. A handful of right-shaped angels is worth more than one wrong-shaped fund, and the right one moves the needle in ways a fund partner with twelve other portfolio companies cannot.

There is a cost on the founder side of all this that rarely comes up in the meeting. Hilary Fenet ran the capital markets business at a large hedge fund before leaving to build Halo. She traded a senior seat in finance for two years of building something on her own, and the gap between those two lives is… wide. (Disclosure: Halo is now a paid sponsor of Long Run Labs.)

There is also a version of institutional money that fits this category, and it is worth understanding what shape it takes, because it tells you what those funds are actually looking for. When I asked Megan where she sees venture actually participating in the outdoor space, she did not point at a single brand. She pointed at the ecosystem. Any one niche outdoor sport may be too small for a financial investor to underwrite on its own. But an ecosystem of them, with enough shared infrastructure on the back end and enough cross-pollination of the same customer between them, can clear a bar that a single brand cannot. The fund is not betting on one shoe company. It is betting on a network of niche communities that share plumbing and share an audience.

The ecosystem bet is one shape institutional capital takes in this category. There is a second, which is the depth-first bet: back what gets proven with the most demanding users first, on the theory that it travels outward from there. The clearest version of this I have heard is the space analogy: build it for the most extreme environment there is, and the materials end up in your kitchen twenty years later. Oura is the obvious recent case. It got adopted by athletes and quantified-self people first, earned its credibility there, and only later became a mainstream health product. That path was venture-funded, heavily, and it is a fair example of what the capital actually buys when the category supports it: the ability to scale hardware and distribution fast enough to own a category before someone else does. No amount of patience (or bootstrapping) gets you there. NEXT Ventures, where I do project work, invests in companies addressing the root causes of poor and disparate health outcomes through whole-person care, and the athlete is where a lot of that gets validated before it reaches everyone else. I am compensated by NEXT, so weigh that accordingly, and this is a description of how they think rather than a suggestion that you go pitch them.

Knowing which of those shapes you fit is more sophisticated than what most founders bring to a raise. If you are a single brand, know that you may be too small for a fund, and that the operator-angels are the better room for you. If you are building something that sits across multiple niche communities, or that could become the shared infrastructure underneath them, you may be exactly the shape a patient fund is looking for. Know which one you are before you take the meeting.

What kind of company actually wins?

The frame that has been working for me here is one I borrowed from Erica Wenger, who runs Park Rangers Capital and published an essay called Elephants Not Unicorns that I keep coming back to. Erica invited me to join as an LP back in 2024. I wasn’t ready then, and the thesis has held up better than I expected.

The unicorn is the venture archetype. Rare. Mythical. Engineered for a single outsized outcome that justifies a fund’s entire portfolio. Erica’s argument is that the next generation of great companies, especially in consumer, will look more like elephants. Large, slow-moving, herd-driven, hard to kill once they reach size. Venture math is built to hunt unicorns. This category mostly grows elephants, which is exactly why so much of the capital chasing it right now is the wrong shape.

The three traits Erica names are the right ones:

• Social attraction, by which she means the company draws members and long-term evangelists rather than buying users.

• Mission first, by which she means the mission does the visibility and branding work that paid acquisition does for a unicorn.

• Building in public, by which she means earning trust through transparency and storytelling rather than through PR cycles and product launches.

The underlying mechanism is that an elephant company owns its own distribution because the customers feel like members rather than transactions.

The endurance brands still standing in ten years will be elephants, and the funds chasing unicorns will mostly miss them. Three founders make the case better than any definition can.

Sid Baptista at PYNRS (disclosure: I am an investor and hold an advisor option grant) is the clearest current example. He built Pioneers Run Crew before he ever sold a shirt. Years of group runs in Dorchester. Empowering leaders. Creating space for runners who did not see themselves in the existing brands. When PYNRS launched in 2020, the community already trusted him. He partnered with Brooks, took creative control of the commercial, and sold through. He removed Black-owned from his marketing because he did not want anyone asking permission to buy his shorts. That is an elephant founder. Identity, community dedication, distribution that compounds.

Rachel Friedline at Wilderdog is another one. Ten years of bootstrapping an outdoor dog gear brand. Over five hundred thousand dollars donated to shelters along the way. Turned down investors because she did not want to dilute the mission.

Kyle Siegel at Raide is the same pattern in a different category. The brand is the product is the founder, and customers feel like part of the project.

I watched this hold up in person. Word of mouth is the engine, and the athletes wearing the product are the proof. That is not a growth hack you can buy. It is the slow, compounding kind of trust that looks like nothing on a CAC spreadsheet and like everything when you are standing in the crowd watching who people actually believe.

What ties them together isn’t just that they own their distribution. It’s that a competitor couldn’t buy their way to the same place. Give a better-funded brand the same product spec and twice the budget, and it still wouldn’t have the community, the founder, or the years of earned trust that produce the social attraction Erica names. That is the real moat: everything on the spec sheet is copyable, and the relationship between founder and audience is the one thing that isn’t.

There is a reason this matters more now than it did even two years ago, and the reason is AI. Megan’s sharpest line on it is that AI accelerates the defensible creators and washes away the rest. When the cost of making a product, a piece of content, a landing page, an entire brand aesthetic drops to almost nothing, the things that are easy to copy stop being worth anything. AI doesn’t threaten the elephant so much as raise the cost of becoming one. When anyone can generate the product, the content, and the launch in an afternoon, the only scarce thing left is the community you spent years building, the one that trusts you by name. The flood of cheap, machine-made everything makes authentic human connection more valuable, not less. Everything else just got easy to copy. This didn’t.

Here is how underappreciated this still is. At the biggest gathering of brands and operators this sport has (TrailCon), the way AI is changing how customers find and research the products they buy was not on a single panel. The industry most exposed to this shift has not yet named it out loud, and that is the tell. It means the founders who understand it are early, not late. The buying journey increasingly starts with a question typed into a model, not a search bar, and what those models say about your brand is becoming as important as what your own website says. Most of the category does not yet know this race has started. But you do, since you read my Centium AI study, right?

How AI Recommends Running Brands in 2026: The Largest Study Yet.

If you are raising, ask yourself honestly. Are you building an elephant? Could a better-funded competitor replicate what you have if they had 18 months and $10M? If the answer is yes, you have a product, not a company. If the answer is no, and the reason is that you have spent years building a community that trusts you specifically, you have a company worth raising for.

What I would tell you if you sat down across from me

If you are raising right now in this space, six things.

• Figure out which category you’re in. The seven-category map is the whole ballgame, and the space is not one fundraising market.

• Decide what you’re optimizing for before you take the meeting. If you want a category-defining brand built on patient compounding, don’t pitch a fund whose model needs an outcome your business was never built to produce. The mismatch won’t show up in the meeting. It shows up in year three.

• Don’t raise before you believe in the business. Kyle’s lesson. And if you’re raising from friends and family, take the money from people you can face if the first year goes sideways.

• Take the meeting with the operator-angels before the institutional money. Smaller check, higher alignment, more relevant help, and the right one often brings a syndicate that makes the effective check bigger than it looks.

• If venture is the fit, find the funds that have done this category and have the patience it demands. Not the ones marketing hardest, the ones with the relationships.

• Build the elephant before you take the capital. Community before product, founder-market fit before fundraise, distribution before scale. The raise accelerates what’s already true. It doesn’t create what isn’t. In a world where AI made everything else cheap to copy, the community is the one part a better-funded competitor can’t buy past.

The honest version

There is a story being told right now that endurance and outdoor is having a moment, that capital is flowing in, that the brands are about to scale, that the next Patagonia is being built. Some of that is true. A lot of it is the same story that gets told about every category right before a wave of bad capital washes through and leaves a trail of broken brands and disillusioned founders. This is the warning that Ian MacGregor (CEO of Skratch) flagged at TrailCon.

The brands that are still here in ten years are the ones that picked the right capital partners early, that knew what they were optimizing for, that believed in themselves enough to defend their own valuation, that owned their distribution because they earned it, and that did not let the model become more important than the customer.

If you are building one of those brands, the room you want to be in is smaller than you think, the capital you want to take is more patient than you think, and the operators you want to be sitting next to are the ones who have figured out what they actually want before the term sheet hits the table.

That is the room I am trying to be in. If you are building toward it too, here is the actual ask.

If you are raising right now, or about to, send me what you are working on. A sentence on what you are building, who it is for, and where you are in the process is enough to start. Founders have reached me both ways, through people I know and through cold emails from people who heard themselves in an episode. The cold email works more often than you would think.

One thing to know going in, because the whole point of this essay is that you should know what you are walking into before the meeting. I am an operator-investor, and I have an advisory relationship with a venture fund, disclosed below. I am not a broker. I do help companies I already advise or have invested in get in front of people I know, but I am not paid to do it. If I read what you send and think you would hit it off with someone in my network, I may offer to make an introduction. What you do from there is between you and them. I am not paid to send you anywhere, and any introduction I make is one I would make whether or not it went anywhere. I do not receive transaction-based compensation in connection with any investment or introduction. I do not negotiate terms, advise on deal structure or valuation, handle investor funds, or participate in any offering.

What did you learn? What did I miss? What else would you add?

Reminder: nothing in this essay is investment advice or an offer or solicitation of any kind. See the full disclosures at the bottom.

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Episodes referenced:

• Seth LaReau, Trailwaves, on the trail running investment thesis. Apple · Spotify

• Cole Zucker, Kila Running, on bootstrapping and venture math. Apple · Spotify

• Doug Waters, Terlingua Threads, on the alignment problem. Apple · Spotify

• Kyle Siegel, Raide, on the fundraising mistake that still stings. Apple · Spotify

• Ryan Hurley, Lagoon, on friends-and-family rounds and finding the niche. Apple · Spotify

• Ross Mackay, Cadence, on building a second brand and the discipline of no. Apple · Spotify

• Randi Zuckerberg on investing in the entrepreneur. Apple · Spotify

• Salomon Aiach on operational discipline and super-fans before casuals. Apple · Spotify

• Sid Baptista, PYNRS, on community before product. Apple · Spotify

• Rachel Friedline, Wilderdog, on bootstrapping for ten years. Apple · Spotify

• Megan Lightcap, SLOW Ventures, on why the creator is the company. Apple · Spotify

• Monica DeVreese (rabbit), Hilary Fenet (Halo), on community and travel. Apple · Spotify

*Recommended reading: Erica Wenger’s Elephants Not Unicorns at Park Rangers Capital.

Disclosures: This essay names companies and funds I have financial relationships with, and you should weigh what I say about them accordingly. I am an investor and advisor in Laurel and a new advisor in Hytro, where I hold an advisor option grant. I hold an advisor option grant in PYNRS and invested in their crowdfunding round. Halo is a paid sponsor of Long Run Labs. rabbit is a consulting client. I write checks personally, not as a fund. I advise NEXT Ventures on a paid project basis. I have no financial relationship with Park Rangers and am not an LP in the fund.

This essay is my personal commentary and opinion. It is for general information. It is not investment, legal, or financial advice, and it is not a recommendation to buy or sell any security or to invest in any company or fund. It is not an offer or solicitation of any kind. This is written for founders, not prospective investors. Do your own diligence and talk to your own advisors before making any investment decision.

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Jon Levitt is the host of For The Long Run, founder of the Long Run Labs Network (35+ shows, ~1M monthly downloads), and co-founder of The Huddle. This newsletter covers the business of creator partnerships, sponsorship strategy, and what the data actually shows, in addition to a weekly article from that week’s Long Run Labs Podcast.