Reading the Terrain: Tana Hoffman Cook on Pivoting Without Losing Your Way

Tana Hoffman Cook has built two companies with five pivots, all while serving the same customer base: women who want to get outside and don’t have the gear, the crew, or the experience to do it alone. The businesses changed shape several times. A gear-rental service became an e-commerce shop, which became an online community, which became an app, which became the single-day adventure company she runs today. The customer and community never changed. That thread, staying loyal to the people you serve even when the business model changes, was the heart of Tana’s conversation at our July Chance Meetings gathering at The Virginian. She talked candidly about supply chains breaking overnight, funding drying up, and the harder pivot nobody warns you about: the one where you take a full-time job and have to ask yourself whether that means you failed. What follows is a lightly edited version of that conversation.

Thanks to The Virginian for hosting, and to Pirate Ship, our legacy sponsor.

Building Mountainist: From Rentals to Revenue

Rebecca Reimers: Tana, you’ve built a few companies and have a deep background in digital content creation. Tell us about Mountainist. How did it start?

Tana Hoffman Cook: Let's go back to 2018. At the time, I was working freelance after TGR, doing content projects, and was a sponsored athlete coaching women’s snowmobile clinics. I noticed an issue: these women could rent machines and helmets, but there was nothing available in their size—avalanche bags were too big, and they were stuck wearing men’s gear. That affected their confidence.

Back then, companies like Rent the Runway and Nuuly were offering women’s clothing on subscription. I decided to try “Rent the Runway for women’s outdoor gear.” The brand I was sponsored by let me buy some gear at a discount. I built a small rental inventory for snowmobiling, dirt biking, downhill biking, hiking, and camping. The gear-heavy activities were most popular.

 I partnered with clinics—if someone signed up, they could get fully outfitted and pick up their gear upon arrival. It was a fun way to serve active women. That’s how it started, but not how it ended.

From Rentals to E-Commerce and the Impact of COVID

Rebecca: You were successful for a long time. What changed?

Tana: See if you can count how many business models show up in this story! At first, I was a coach, then I added rentals. But after clinics, women would ask, “Can I buy this gear?” There was more money there. So I reached out to brands and asked to become a dealer. Because of my relationships, I was able to build an e-commerce site, and within two months, we had five-figure monthly sales—including orders from Canada. Rentals became a lead generator, introducing women to the sport and then outfitting them fully.

Then, in 2020, the pandemic hit. There was an initial surge—everyone wanted to be outside. We sold out of everything, and then the supply chain broke down. Most brands shipped from overseas, and as a small shop, I couldn’t get more inventory while big sites like Backcountry or RevZilla still could. The business essentially shut down except for a few rentals.

Rebecca: I remember you being super resourceful—getting grants and keeping things going.

Tana: The hardest part was the lack of control. Usually, you can solve problems with creativity and grit, but suddenly, everything cost double. So, we asked: how else can we serve this community? My team and I created a Facebook group to introduce our customers to each other. We hosted online workouts and events—creating community without inventory. For about six months, that gave us a sense of purpose.

From Community to ILLA Adventures

Rebecca: How did that flow into your next venture?

Tana: This community—only about 400 or 500 women—helped each other find friends and adventure partners. A friend saw what we were building and told me about an accelerator looking for startups in outdoor brands. I pitched a new idea: a digital community where women can connect to meet up outdoors. We called it the Mountains Collective, later rebranded as ILLA.

We received funding to build an app. Users could say, “I want to go biking on Saturday,” and it would invite all members within 100 miles, at their level, to a group chat—sometimes just one other person, sometimes a dozen. We grew to 3,000 members, organizing hikes, surfing meetups, and more. The core remained: serving women in the outdoors, now as a membership-based digital community.

Lessons from the Pivot

Rebecca: What did you learn from Mountainist that helped you with ILLA?

Tana: Meeting customers face to face at events and clinics was invaluable. I learned about their dreams and their obstacles. That translated to the app—finding ways to help women feel safe and connected even when meeting a stranger for a hike. Duplicating that in-person community feeling online was key.

Rebecca: Fast-forward to now—there’s been another shift, both for ILLA and in your own career.

Tana: ILLA was taking off in terms of engagement, but the membership model didn’t scale as well as we needed—ad-based models are tough in niche markets. When funding dried up, I needed stability for myself and got a full-time job as a creative producer, running global events and business programs. That "oxygen mask" moment gave me back my creative bandwidth.

Three weeks after accepting the new job, I started having fun again—organizing an event for snowmobiling through ILLA. It sold out in nine minutes. Now, ILLA Adventures focuses on single-day adventures for women via local operators. We’ve introduced over 200 women to sports—wake surfing, dirt biking, climbing, mountain biking. While I haven’t sold for billions, it feels exactly right for this community and for me.

If there’s a lesson here, it’s this: Be quick to kill the product, but never kill the customer. Stay loyal to the people you're serving, not just the idea. If you’re tracking, there were five business models, but always the same core audience. The art of the pivot is resourcefulness, adaptability, and remembering who you’re doing it for, not what.

On Situational Awareness and Courage

Rebecca: It takes courage to pivot—it’s hard to let go of something you’ve built. Where does your honesty about what’s working come from?

Tana: I think it’s less about knowing if the product is working and more about staying situationally aware—watching for what deserves your attention, not just what you planned to do. Outdoor athletes understand this: situational awareness is everything. It’s not about fixating on the door and missing a window opening somewhere else.

Rebecca: Failing faster, having courage, knowing your audience—what other hindsight lessons stand out from all these twists and turns?

Tana: We don’t talk enough about the personal pivot—how much our identities get wrapped up in what we do. When I decided to get a job, I wondered, “If I’m not a founder, who am I? Does this mean I failed?” Now, I realize it’s crucial to have an identity outside of what pays you. Whether it’s hobbies, sports, creative work—whatever sustains you apart from your professional profile.

I encourage everyone, especially founders who feel burned out or stuck, to find structured hobbies—something with a learning curve and real engagement, not just self-care in the “bubble bath and candles” sense. Create environments where you own an identity beyond your achievements, and build community from that. That’s where creativity and resilience live.

Rebecca: At Silicon Couloir, that's something we emphasize—teaching the founder, regardless of their business’s trajectory. It’s about skills, leadership, and moving through life intentionally.

Audience Q&A

Audience: How do you know when to pivot, especially if you’ve already tasted some success? Is there a formula for when to let go and try something else?

Tana: If I find that exact formula, I’ll bottle and sell it! But seriously, think of heading down a mountain—there might be a goat path you always take, but the best powder might be in the trees. You need the courage to explore where your instincts or observations lead you. The key is to stay alert and experiment—ask your audience, host events, float ideas, and see what resonates. These are the breadcrumbs that guide your next move.

Audience: How has the experience of writing been for you? Did you have a writing background?

Tana: I’ve always been a copywriter, mostly for sales and conversion. I started writing more intentionally as a way to process transitions, share what's on my mind, and see what resonates. That’s how some of our events have grown—sharing my own experiences, getting feedback, and converting that into action. Writing has felt cathartic, and now I’m even working with a book coach. You can read some of my recent work at tanahoffmancook.com.

Audience: I have three daughters, all athletes, in business and building families. Do you have thoughts on balancing these pivots while raising a family?

Tana: I’m not a parent, but I have many friends juggling that transition. I always say: treat yourself like your most important client. Make time for what lights you up, and find creative ways to weave those passions into your life—sometimes that means starting new communities or inviting others in. Even minor activities can be a lifeline for identity and growth.

Audience: The Wonder Institute is a great place to try new hobbies and find community outside of work—I recommend everyone check it out.

Tana: Exactly. Hobbies aren’t just a side pursuit—they create momentum, introduce you to new people, and often lead to unexpected opportunities and creative breakthroughs. For me, there’s a cycle: I dive into a hobby, meet new people, find new opportunities, and then come back to the hobby to reset. If you’re stuck, go try something new—you never know what door it’ll open.

Audience: You’ve experienced both lifestyle and venture-backed businesses. How do you think about those paths?

Tana: I started Mountainist bootstrapped, and it worked until COVID. ILLA was venture-backed, and I thought I wanted the big “unicorn” play. But the process taught me that isn’t necessarily what I want. I’m grateful my investors supported a transition—I now thrive running ILLA as a lifestyle business, working as a producer, and having time for creative and outdoor pursuits. It’s founder-specific, and I don’t think you know which lane suits you until you try both.

Closing Thoughts

Rebecca: Tana, thank you for your vulnerability, honesty, and wisdom. You’ve captured the heart of the pivot—the courage to serve your community, reinvent yourself, and own your journey.

Don’t forget to check out illaadventures.com and tanahoffmancook.com for more about her work and her writings on pivots, identity, and creating an intentional life.

If you enjoyed this, pass it on to a friend in transition who could use intentional, lived wisdom—without the hustle-culture clichés.