When wildfires overtook a wide swath of northern California in 2017, Caitlin (Looney) Landesberg’s parents offered up their farm to local equine owners in need of a spot to house their animals. In the midst of those first rescued animals was a “firecracker” of a burro whose owner ultimately couldn’t reclaim her. “She was stubborn and full of spirit, and she could run,” said Landesberg ’05. “We named her Lucy, short for Lucifer.” With an accomplished background as a trail runner, Landesberg decided to coax Lucy out for a run, intrigued by the sport of burro racing, which she had heard so much about. “We started running with a California burro running team,” she explained. 

Burro racing has its roots in Colorado, where rumor has it a couple of miners grabbed their pack mules and sprinted to the location of discovered gold, in a true winner-takes-all contest. No one knows how that turned out, but a sport was born out of the lore and today, hundreds of runners lead burros through races of varying lengths in locations across the state. The burros each wear a full pack and a harness, and runners cannot ride the animals at any point. Instead, they cajole their four-legged partners to the finish line. 

As her name indicates, Lucy is not always the easiest running partner, especially not in a race. “We’ve spent 15 minutes negotiating a puddle,” laughs Landesberg. 

Anyone who has the patience to run with a stubborn donkey probably has the patience to launch a business, too. In the case of Landesberg, that proves true. A successful entrepreneur, angel investor, mother and so much more, Landesberg has combined what she learned at Kenyon with a rare tenacity to make a lasting impact on the world. 

Step 1: Hit the ground running.

There had to be a “Gatorade of beer” out there somewhere — a beverage that was both refreshing and nourishing post-run — at least that’s what Landesberg assumed. But no matter where she turned, it just didn’t seem to exist. So the trail running, startup finding, gluten-free vegan set out to create her own. 

That’s the abbreviated version of how Landesberg launched her own specialty beer label — Sufferfest — back in 2016. The longer version involves a circuitous career path with a firm foundation at Kenyon, where Landesberg studied English, played tennis and, unbeknownst to her, began building a future that would connect her passions for fitness and business.

To understand how Sufferfest came to be, however, it pays to go all the way back to where Landesberg was born and raised: Silicon Valley. “After graduation, I wanted to get back to San Francisco, and so I joined the communications team at Adobe to help with macromedia,” she explained. “It was a great job and I stuck around for about two years, before leaving with a colleague to work on a startup in the mobile communications field.”

While the startup ultimately failed, it delivered Landesberg a full slate of new and useful skills that have carried her throughout her career. “It was a great experience to jump in, wear multiple hats and build my resume as a marketer,” she said. 

That experience, in fact, led to her next career building block, a stint as product marketer at Mozilla Firefox. As part of the development team at a time when SMS was the latest and greatest, Landesberg traveled the world marketing Firefox on tablets, phones and more. “It was an exciting time,” she said. “I gained a background in community building, developing a brand and marketing.”

Around the same time, Landesberg went for her first trail run in the nearby Marin Headlands, a veritable runner’s utopia best known for scenic views of the Bay Area and Golden Gate Bridge.  While she’d been an avid tennis player at Kenyon, the time and money the sport required didn’t fit into her current lifestyle. So when a friend invited her to try trail running, she gave it a go and never looked back. 

Running on dirt became Landesberg’s passion, and soon she was entering a variety of races, everything from the classic Dipsea in San Francisco to longer “ultra” races, which ranged anywhere from 50 kilometers to 50 miles. Scott Thielke, Landesberg’s tennis coach at Kenyon, isn’t surprised that Landesberg turned to running. “She was always one of the fastest members of the team on court,” he recalled. “She covered the court very well.” 

Landesberg was hooked on the trails, and soon began tracking her miles through another new startup, a social and endurance training app called Strava, created by good friend Michael Horvath, CEO. In 2012, Strava became Landesberg’s next career move. “I loved this job — it combined my passion for marketing and my joy of running,” she said. “As an early employee, I helped out the marketing function, growing Strava from thousands to millions of users during my time there.” 

While trail runners love to check in on their training and racing stats, they also like to commune over a good beer when the day is done. A longstanding tradition, the shared beer serves as part celebration, part method for getting in a few calories and nutrients to jump-start the muscle recovery process. “The influence of being a part of Strava really pushed me with my racing,” said Landesberg. “As I got more into racing, I discovered that beer is intertwined with trail running culture.” 

New to exploring beer, Landesberg developed a keen interest in the ingredients, flavors and alcohol percentages in the many varieties introduced at races. As a vegan with Hashimoto’s disease (a thyroid condition) Landesberg found that many types didn’t work for her, mostly due to their gluten content. “Sometimes it gave me trouble, or had more alcohol in it than I wanted,” she explained.

What was missing from the beer scene, in Landesberg’s opinion, was a lifestyle beer for athletes. “Every time I ran a race, I’d bring a grab bag of beers from home and I started concocting my own versions,” she said with a laugh. “I became a specialist of beer without really thinking about what I was doing.”

Then came a birthday present from her husband, Stuart, that changed the course of her life. “Stuart bought me a beer-making course and kit,” she explained. “I wasn’t thinking about making a profit from beer, but I did bring the lens of an athlete looking for a beer fortified to my needs.” The birthday gift led to a more intensive beer-making course at U.C. Davis, where Landesberg learned from beer masters how to craft specialty brews. “It was all still a fun hobby, but I was dead set on creating something I could share with my athletic friends,” she explained. In other words, Landesberg was on her way to creating that “Gatorade of beers.”

Step 2: Take a calculated risk.

Thus began a period of trial and error, adding this/removing that until Landesberg came up with the ultimate recipe that not only tasted good, but checked the nutrient boxes she felt were missing from existing brands. “Our first brand promise was that our beers would be gluten-free,” she explained. “Early on, I used a barley adjunct (like sorghum, soba or rice) to brew my beer. However, the taste and mouthfeel never delivered for me. I wanted to have an amazing-tasting craft beer (that I could drink) and never settle, which led to all of my beers, in perpetuity, to be gluten-removed.” 

Landesberg accomplished the gluten removal by creating a barley-based “conventional” beer, removing the gluten using an enzyme during fermentation. The end result was a craft beer brewed perfectly to her desired specs. “To my gluten-free friends and me, beer was back,” she said. 

The second part of the process involved adding in the nutrients Landesberg wanted as an athlete. “I wanted to know if beer could be fortified,” she said. “Could certain minerals, additives, ingredients and adaptogens be soluble in beer?”

At first, her creations were far too salty, she said, as she experimented with electrolytes, and too tangy as she included “super food” add-ins. “As my recipes improved, and I found more balance in my beers, the biggest hurdle was using ingredients like bee pollen, collagen, activated charcoal and other, trendy and goal-specific ingredients that were FDA-approved in an alcoholic beverage.” 

Landesberg’s first offerings included the Flyby pilsner and Taper IPA, and she began sharing them with friends at races, parties and group runs. Receiving positive feedback on what Landesberg calls her “happy accident,” a new category of beer was born — functional beer — all while she continued with her duties at Strava and running the ultra-marathon races she loved. 

Finally, she reached a tipping point — she could stay in her current job or leave and pour everything she had into launching her beer brand. As with everything leading up to that moment, Landesberg went for the more challenging choice. “This felt super risky,” she said, “but I had recently married and was able to be on my husband’s health insurance. We had no children but knew we wanted to start a family in the not-too-distant future. It felt like now or never.”  

As with any new business venture, Landesberg’s was not without naysayers. “People laughed when I said I wanted to develop a beer for athletes,” she said. “But this was a massive, unseen market and by six months, it was clear we were onto something big.” 

Step 3: Scale up. 

As buzz increased around Landesberg’s beer, in 2015, she departed Strava, bought a van and took her show on the road. “I decided to give myself six months to continue to develop the beer and prove the concept,” she said. “I went to many races, not as an athlete, but to serve beer and spread the word.”

She also started bringing samples to local grocery stores and beer stores, which required her to license her brewery and develop a label. “I walked up and down the streets of San Francisco with a cooler full of beer, not knowing what I didn’t know,” Landesberg said. The learning curve was steep. 

“As a tech marketer starting a brewery, I was as far away from my comfort zone and core competency as I could be,” Landesberg said. “One of my bridesmaids designed my label as a wedding gift — it didn’t even occur to me that I had to be a licensed producer and hold an approval label.” 

For awhile, Landesberg ran Sufferfest Beer Company out of a guest room in her 900-square foot San Francisco apartment, which required her to add a “notice of alcohol establishment” sign on her front door. “I’m pretty sure my neighbors thought I was running a speakeasy,” she said, laughing. 

Landesberg set her sights on some of the bigger retailers and by May 2016, she had successfully landed Sufferfest in all 42 northern California Whole Foods stores. “Initially I sold to each store individually, but I started to get the attention of the regional manager, so I knew it was worth pursuing bigger accounts,” she explained. “About six months in, I hired my first full-time sales rep and together we opened about 200 doors in California.”

Funding came next and Sufferfest “took over California,” said Landesberg. As a pioneer in the beer world, creating the first true functional beer, she began drawing a good deal of attention.

In a 2019 interview with Runner’s World magazine, Landesberg said she first heard the term “sufferfest” at Strava. “We were developing this product called a suffer score, a premium product for mostly cyclists. If you put our formula together around miles and time and output you’d get a suffer score,” she said in the profile. “We do the same thing for running in terms of elevation gain/lost, time, mileage. We give you a suffer score, basically showing how hard you work. I think it’s certainly been a term of endearment that I’ve heard within the context of endurance.”

In the midst of building a successful new category of beer, Landesberg and husband Stuart had their first baby in 2017, followed by their second child in 2019. While eight months pregnant with her youngest in 2018, Landesberg spoke about marketing at a beverage conference in Los Angeles. “I was the only female in the audience, and no one knew that I would be presenting,” she said. “After I talked, Jeff White, the CEO of Sierra Nevada, reached out to me to compare notes and share ideas.” 

Sufferfest operated as a B-corp (benefits corporations that make positive impacts on the community) and shared many synergies with Sierra Nevada. “They are a leader in social and environmental stewardship,” she explained. “They are LEED certified and they have focused incredible amounts of time and resources to make their breweries closed systems.” 

While Landesberg and White discussed potential collaboration, ultimately, Sierra Nevada acquired Sufferfest so that as one, they could continue to accelerate innovation and lead functional beer nationwide. For the next 18 months, the entire Sufferfest team worked under the Sierra Nevada umbrella, integrating systems, updating packaging, optimizing their portfolio of beers and rolling out nationally in February 2020. 

As quickly as the Sufferfest star rose, the pandemic dealt the business a fatal blow, even while under the bigger shelter of Sierra Nevada. “COVID was closing down retailers left and right,” said Landesberg. “While alcohol consumption might have been up at this time, new brands like ours were unable to visit stores and offer samplings and events, or to sell our product.” 

These were dark days for Landesberg. “I lost my business due to the pandemic,” she said. “I lost people close to me. On paper, it was the worst time in my life. Upon reflection, however, I spent 2020 and 2021 with those I love most.” 

Step 4: Take a breath and recalibrate your goals.

If you haven’t figured it out by now, Landesberg doesn’t sit still for long. “I get nervous if I’m not busy,” she admitted. “But after leaving Sufferfest, I wanted a year to spend time with my family, observe and listen to what my next step should be.” 

Until that moment, Landesberg had “always had a day job,” she said, and this was the first time she had stepped back and paused. It was a daunting task for someone always on the move, but a worthwhile one. Her daily life took on a different pattern: sharing walks with her mom, having dinner with her young children and prioritizing personal over professional. “It was an enormously valuable awakening for me,” she said. “To me, it was a gift of time, one of my most transformative periods in life.” 

Landesberg’s reflection time led to her present endeavor, serving as an angel investor under the banner of This Is Water, LLC. In this role, Landesberg helps seed alternative packaging for beverages and consumer goods, advance alternative meat options and focus on women’s health issues. “These are my social passions,” she explained, “and I’m focused on funding companies that are leading the charge in those areas.”

In a “pay it forward” manner, Landesberg has shared her learnings and experience with other entrepreneurs. “Investors had to take a chance on me in order to grow Sufferfest,” she said. “I was suddenly in the fortunate position to do the same.” 

About the “This Is Water” name Landesberg landed on for her investing ventures: you can trace it back to her 2005 Commencement at Kenyon, where author David Foster Wallace delivered a seminal speech by that title on the conscious awareness of others. It left an impression. “I think all of us sitting in that audience started to understand the power of his words and its message as he was speaking to us,” Landesberg said. “Wallace was struggling. We were all struggling. Simply put, the human experience is hard for every single one of us.”

Wallace’s message, said Landesberg, was that everyone has the power of choice and the ability to choose how to see the world. 

Recently, Landesberg has enjoyed reconnecting more with her alma mater. “I love Kenyon; it’s a place like no other,” she said. “But until I finished with Sufferfest, I hadn’t given much back to the school. Now I can.” Her efforts include joining the campaign leadership committee to engage younger students to think about their contributions to Kenyon. 

As she rides out the pandemic with the rest of us, Landesberg chooses to focus much of her attention on taking Lucy the burro to Colorado to join in the bigger, more official races, to see how things go.  There’s no doubt that with Landesberg’s track record, she and Lucy will do just fine.

Bottoms Up: Playing Favorites with Caitlin Landesberg '05

Best business advice you've received, and from whom?

“It’s not your job to be right. It’s your job to move the business forward,” was said to me by an advisor and it immediately shifted my lens. I learned that part of being a good CEO was to check my ego at the door, admit when I didn’t know the answer, get mud on my face and fall on my sword. Humility and discipline ultimately became an enormous strategic strength. 

Favorite beer right now?

Moonlight Brewing’s Reality Czech

What is your favorite trail race of all time?

The Double Dipsea is my favorite because it was my very first trail race. It’s a scratch start by age group so everyone in theory has a chance to win — whether you’re 17 or 71! 

Is there a charity you like to support?

Cancer Commons is an organization for advanced cancer patients to get second opinions on their diagnosis, and learn about the most cutting-edge drugs, treatments and clinical trials available. My mom was a client, and in her legacy, I have underwritten an educational series so that more people can take advantage of such an incredible and empowering resource. 

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