Nobody Is Talking to the Middle of the Pack. Rabbit and Halo Think That's the Whole Business.

At TrailCon this year, Alyssa Olenick, PHD described her own audience out loud, and then shared some sharp and astute commentary. Roughly a quarter million followers on Instagram, almost all of them mid to back of the pack. Her point was that almost nobody is speaking to those people.

They are also, statistically, most of the sport. They buy the shorts, book the flights, pay the entries, and fund the brands that spend their marketing budgets on the front of the field. I sat down in Lake Tahoe with two founders who have built their entire businesses around that runner, and who have a partnership with each other because of it.

One disclosure before we get into it. This conversation was recorded a few weeks before there was any business between us. Since then Hilary and the team at Halo have come on as a partner of the show, and that happened because of conversations exactly like this one, not the other way around. You’ll hear a proper word from Halo starting next week. Today the conversation stands on its own. I’m also now working with rabbit on a separate project, which I’m sure I’ll write about in the future too!

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Who: Monica DeVreese, CEO and co-founder of rabbit

Where: Santa Barbara, CA

Day job: Running ten years of a self-funded apparel brand, plus Santa Barbara Running, the shop she and her husband own

Runner notes: Was in Tahoe to crew and pace her training partner at Western States

Who: Hilary Fenet, founder and CEO of Halo

Where: New York, NY

Day job: Building the booking and community layer for race travel, two years in, still not taking a salary

Runner notes: Picked up trail running in Cape Town in 2019, then spent years traveling to races out of a city with almost no trail scene

Monica’s path is the one a lot of people in this industry recognize. Team sports, then running, then a career inside the brands, then a running shop with her husband. Standing in all three positions at once, as consumer, as brand operator, as retailer, is what surfaced the gaps. rabbit came out of those gaps, and the name is the thesis: in a race, the rabbit is the pace setter, the one who gives up their own result for the benefit of everyone behind them. Ten years in, the company is still self-funded apart from three early angels.

Hilary came at it from the other direction. She was an investor at a large hedge fund running the capital markets business, mostly consumer and tech, and she got into trail running while living in Cape Town. When she moved to New York she started traveling to races and kept hitting the same wall: a GPX file open next to Airbnb next to booking.com, trying to work out which side of a mountain to sleep on. Then she’d arrive to find every runner she wanted to meet scattered across a dozen different hotels. Over one Christmas holiday her sister asked why she didn’t just start a company. She took a sheet of yellow construction paper off her niece’s art table, disappeared for an afternoon, and wrote the plan.

Here’s what stuck with me.

I asked Monica directly why so many brands miss that group when the group is the market. Her answer was that the mid-packer is not the shiny object. Attention goes where the screen goes, and the screen is full of elites and creators.

She was blunt about who rabbit actually sells to. The majority of their consumer is that person. The clubhouse concept exists for that person. And Hilary’s observation from the outside was that plenty of brands are running similar hospitality plays this year, they’re just running them for influencers and sponsored athletes.

There’s a version of this that reads as charity and a version that reads as math. This is the math version.

Halo’s insight is almost annoying in hindsight. A traveling runner spends three or four days in a destination. They spend a couple of hours at the expo, one hour at a shakeout, and the rest of the time in a hotel that has nothing to do with the race.

So Halo turns the hotel into the venue. Branded booking, then swag at check in, an early breakfast that exists before a 6am start, a mixer, a shakeout from the lobby, pre-race strategy calls so people know each other before they arrive. rabbit layers its own personality on top of that: hoppy hours, post-race stretching, poster stamping, a croissant making class at the Chamonix clubhouse (and perhaps something else I’ll be cohosting!), and in New York they’re working on bringing in an author to run a writing workshop for the weekend.

I asked Hilary why nobody had done this. Her answer was unglamorous and probably correct. The back end of hotel booking is antiquated, the logistics are miserable, and brands who try a version of it once usually decide never again. What you get instead is a “recommended hotel” link, which is proximity, not hospitality.

Monica’s framing of what Halo adds for a brand going somewhere new was the practical one. For UTMB, rabbit has never operated in Chamonix. Halo’s answer to “where should the clubhouse be” is worth more than the software.

I’ve said on the show before that you can walk down Newbury Street during Boston Marathon weekend, swap the logos between activations, and nothing changes. Everyone is running a shakeout. The Mount to Coast Double Boston worked because no other brand could have credibly done it.

Monica said this is a constant internal conversation at rabbit. Her answer for what makes it uniquely theirs isn’t a tactic, it’s a posture: we show up as your friend, we care about you, come in the door. The quirky stuff follows from that. Bracelet making isn’t novel anymore, but as she put it, ACG isn’t doing what rabbit is doing.

Hilary, who has no marketing background and says so, made the cleanest business case for it. She thinks about lifetime value. An in real life memory attached to a brand converts differently than an impression on a screen, and the example she reached for was ACG’s vertical kilometer at UTMB last year: race to the chapel, coffee at the top, demo their shoes, PR on the descent, friends everywhere. She still hasn’t bought anything. She still remembers all of it.

I ran the math on ACG’s Broken Arrow weekend and landed somewhere near a million dollars. Staff, lodging, race sponsorship, the prize purse, the branding, the tram, buying out Coffee Bar and Slot Bar, the open bar.

Both of them thought it was good for the sport. Monica’s honest first reaction was competitive frustration, which she volunteered without being asked. Then she met Mark, the GM for North America, talked with him several times, and came away thinking he understands the responsibility of the position. I had the identical experience meeting him and came away surprised in the same direction. Hilary’s read was that the details were excellent, the elite experience was well funded, and the rest of us weren’t forgotten, and that the real effect is pressure on Hoka and On to raise their own game.

The harder question came from Ian at Skratch on a panel earlier in the week. Suppose a brand has allocated a few hundred million to trail and draws it down across races, athletes, and media. Suppose it runs out, or the experiment ends. Nike Trail has stepped in and stepped back out before. Does that capital raise the floor of the sport permanently, or does the floor fall out with it?

Neither of them had a clean answer, which felt like the honest response. Monica pushed back on the framing a little by pointing at the events with long tenured sponsors, Javelina among them, where rabbit has been the apparel sponsor for seven years and Hoka the footwear sponsor. And a stat that circulated at TrailCon, that the average US race has around 60 participants, got skeptical treatment from both of them. It seems like a long tail (median) being reported as an average.

Monica is a self-described spreadsheet person who lives and dies by cash flow. rabbit has never done a real raise. She’ll acknowledge the cost of that openly: they control their own destiny and grow at their own rate, and they may be leaving opportunities on the table. What she can’t do is run a six figure monthly burn. Her definition of success came out as three things, in this order: consumers who love the brand, a company that lasts a long time, and employees whose careers get better for having worked there.

Hilary is running a software business into a very large travel market, so the calculus differs. She bootstrapped first, still doesn’t pay herself, and raised from angels who are mostly trail running friends who have exited businesses. Her filter has a name: FLO, fucking legends only. I’m going to use that in the future. Be picky about the cap table.

Her best tactical advice for founders considering a fund was the one I hadn’t heard framed this way. Look at the fund’s portfolio and ask whether those companies could be your customers. If yes, you’re buying capital and distribution with the same check. Then call other portfolio CEOs before you sign, since the roster is usually published on the fund’s own site.

The mindset piece came from her advisor Courtney Dauwalter, who she says never talks business with her, only mindset. During a grinding seed process, the advice was to think in tiny grains of sand. Stack small things until they’re a mountain, rather than staring up at the mountain. And there’s the Mark Cuban line I brought up from Erica Wenger’s Trailblazers podcast: raising money is not a measure of success; it’s an obligation.

The part of this I want to flag for founders is that the whole discussion of “bootstrap or raise” skips most of the actual options. In about four minutes the three of us listed bank debt, convertible notes, pre-orders, and C2FO on the wholesale side, where you concede a point or two of discount to get paid early by a large retailer and close the inventory cash gap.

The reference points are worth chasing down. Shoe Dog is a bank debt story from before growth capital existed. Todd Graves at Raising Cane’s went a similar route and still owns most of it. And the Costco cash conversion cycle, which Acquired covers well, is a business where suppliers effectively float the company’s working capital.

Halo is already working in college sports and getting pulled toward golf. Hilary’s stated ambition is the booking.com and Expedia tier of the travel market, approached through sports, with running as the proof point.

Which brought us to a thread I keep pulling on. I have a network of 35 shows, and nobody travels more than runners. So why are airlines and hotels not in running media and running events? Hilary’s answer was market size, that running is still small next to what those advertisers usually buy. But London just announced 100,000 entrants, and as she pointed out, every one of those runners brings people. The traveling party is several times the field.

• The mid-packer is the P&L. rabbit’s majority customer is the runner nobody is marketing to. Brands chase the podium because the podium is what looks good on a screen.

• Lodging is unclaimed inventory. Runners spend three or four days in a destination and most of it in a hotel with no relationship to the event. That’s the largest block of unprogrammed attention at any race.

• Differentiation is a posture, not a tactic. Everyone can run a shakeout. Only rabbit can do the thing that reads as rabbit, which is why Monica frames it as showing up as your friend.

• Big brand capital is a real question, not a talking point. Ian at Skratch’s version is the right one to hold onto: does the money permanently raise the floor of the sport, or does the floor leave when the money does?

• Bootstrap first, then be ruthless about the cap table. FLO. And check whether a fund’s portfolio companies could become your customers before you take the check.

• Monica on LinkedIn · rabbit at runinrabbit.com

• Hilary on LinkedIn · Halo at poweredbyhalo.com

• Clubhouses this season: Chamonix for UTMB, the Walker Hotel for New York, the Arlo for Chicago.

The Huddle. Building a business is isolating. You’re making decisions daily that most people in your life don’t fully understand, and surface-level networking rarely helps. What my co-founders Jason Fitzgerald, Ross Yellin, and I built at The Huddle is different: a peer advisory community for early-stage founders who want real accountability and real conversation. Small cohorts, cross-industry, monthly sessions. Someone in the room will tell you the thing you actually need to hear. In-person in Boulder, virtual cohorts open anywhere. Go to findmyhuddle.com and fill out the application.

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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.