Life Begins At The End Of Your Comfort Zone

Bouncing Back from the Brink: 5 Lessons on Grit and Pivoting with Jess Lynch

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At just 32 years old, Jess Lynch has already lived the full entrepreneurial experience. She successfully founded, grew, and sold a startup, weathering storm after storm as she built a technology company up from scratch. Today, as Founding Partner at Raiz Capital, she helps coach other founders on their own journeys of grit and growth. Pete Sena and David Salinas recently had the pleasure of speaking with Jess on the Forward Obsessed podcast, where they covered the highs and lows behind growing a business, surviving pitfalls, pivoting again and again, and finding a path forward to getting acquired. Her story of repeatedly overcoming the verge of failure was profoundly inspiring.

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During our conversation, Jess shared hard-won insights on the tenacity required as an entrepreneur. We distilled her wisdom into five key lessons that any founder can apply when they reach their darkest hour:

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Persevere Through Self-Doubt and External Challenges

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The entrepreneurial drive was baked into Jess from an early age. As a third grader, she excitedly told her parents in the car after school about her first business idea - breeding hamsters to sell to other kids. Though Jess drew up an enthusiastic business plan to convince her parents, they wisely recognized her lack of passion for caring for the animals. Still, they encouraged her creativity by buying Jess a single hamster. When she proved frightened of the hamster itself, Jess quickly realized the idea would not work, leading to her first failed business venture. However, the experience still planted an early seed that Jess would continue watering in later startups. Even ideas that do not fully blossom still provide learning to fuel future success.

Later as a founder, she battled through many external challenges that would have broken less determined entrepreneurs. At one point, after countless fruitless attempts to gain traction during the pandemic, she considered whether it was time to give up. "I literally was googling when to give up. how do you know as a founder you should quit?"

When facing the option to quit, Jess referred multiple times in the interview to the importance of listening to her inner voice and intuition. During the darkest days of the pandemic, as Wishroute hemorrhaged money, Jess said she had to “look inward” to decide if she should keep pushing forward or walk away. She leaned heavily on her meditation practice, which she believes helped connect her to her "gut" and inner wisdom. Ultimately, an inner spark kept telling Jess to persevere, that something hopeful waited on the other side if she could endure a bit longer. While always a believer in data and customer feedback, Jess found that tuning into her own internal compass gave the final guidance necessary in times of deep uncertainty. Her self-trust proved warranted, as Jess went on to successfully sell Wishroute just a couple years later.

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The key insight: As an entrepreneur, you’ll likely battle self-doubt and face external crises that seem insurmountable. But you must believe in yourself and your mission. Let tenacity and intuition triumph over tribulation.

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Pivot Fearlessly When Forced to by Circumstances

No amount of perseverance can overcome existential threats completely out of your control as a startup. When COVID-19 hit the world by storm, it demolished industries like fitness that Jess had tailored her product Wishroute toward. She recounted the constantly foiled attempts to gain any traction at the start of the pandemic; "We kept trying new pitches to gyms or fitness studios or other online communities to host challenges to help people lose weight or stay accountable to a program.” The problem was, COVID 19 was shutting down all gym activity across the company, and her idea just wasn’t a viable option anymore.

Most businesses would have collapsed under those headwinds. However, Jess pivoted yet again, finding creative ways for Wishroute to continue empowering people to build healthy habits. Jess and her team began brainstorming creative pivots, rapidly iterating on new ideas to provide value amidst the chaos. They pivoted to hosting virtual health challenges, partnering with individual health coaches, even providing mental health support specifically for frontline nurses. Some launches succeeded while others fizzled, but each informed the next. After months of experimentation, Jess ultimately transformed Wishroute's model to integrate directly into health and wellness apps' own experiences via white-label partnerships. By doggedly continuing to pivot despite the constantly shifting pandemic landscape, Jess was able to morph lemons into lemonade and set Wishroute on a brand new path toward its eventual successful exit. By pivoting fearlessly, Jess turned the seeming end of the road into just another bend.

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The key insight: As external factors shift, stubbornly sticking to your approach can sink your startup. Pivot boldly instead–adjust your sails to the winds of change.

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Lean on Your Network in Times of Crisis

Jess vividly remembers the sleepless nights as Wishroute's bank account dwindled dangerously low. To cover payroll, she and her husband began paying employees out of their personal savings, watching the balance drain week after week. Emotionally, Jess described the period as an intensely scary and challenging time, full of tears and self-doubt. She knew the jobs of her team depended on her leadership, yet Jess admitted to feeling broken, overwhelmed by the weight on her shoulders. With just a few weeks of savings left to burn through, Jess stood on the precipice of having to shut Wishroute's doors permanently.

Rather than let resignation set in, Jess tapped her network, speaking candidly about her cash crisis with investors and mentors. One professor and investor who had convinced Jess to start Wishroute in the first place provided pivotal advice - go back to your investors, lay out the facts transparently, and gauge their ongoing belief and willingness to fund the company further. Jess took his advice, and was stunned when investor after investor pledged additional capital, often five or ten thousand each. Within weeks, Jess raised hundreds of thousands in bridge financing, saving Wishroute from the brink. By opening up about her vulnerable position, Jess gave her network a chance to come to the rescue. The experience proved the value of community above all else.

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By opening up to her network instead of hiding her struggles, Jess raised emergency funding to keep Wishroute alive. Her vulnerable conversations rallied her supporters to have her back when it counted.

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The key insight: Don’t wait for a crisis to start building your community. Lay that foundation early on, so you have deep reserves of strength to draw from when you hit your own low points.

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A Messy Cap Table Leads to a Strong Support Network

Entrepreneurial orthodoxy often advises startups to be stringent gatekeepers regarding their cap table, limiting investor entry to maintain control. However, Jess Lynch gleaned an alternative perspective from her experience growing Wishroute. Despite warnings from peers, Jess ended up accepting capital from over 50 different investors. As Jess acknowledged, "I gotta say, people advise you don't want a messy cap table." While navigating the feedback of so many stakeholders did prove challenging at times, the trade-off came in the form of a powerful support squad. Jess explained that, "It was an amazing network to have invested in me." When Wishroute needed to quickly identify and hire rockstar talent for a Head of Operations role, Jess simply activated her cap table, allowing her to tap into the networks of dozens of investors. Within just weeks, she found the perfect candidate through introductions.

Rather than cling to the conventional startup wisdom she initially received, Jess remained open-minded regarding her cap table strategy. By resisting the temptation to limit investor entry, even when it meant sacrificing some control, Jess empowered herself with an invaluable pool of connections and talent. Other founders can similarly think creatively about the strategic benefits investors provide beyond capital. As Jess suggested, "Think beyond just the funding when considering investors for your startup journey." The relationships seeded on your cap table may unlock game-changing network effects.

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The key insight: Think beyond just the funding when considering investors for your startup journey. Look for strategic value-adds that your future cap table can provide.
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Pay It Forward and Lift Up Other Founders

After weathering countless entrepreneurial storms on her journey scaling Wishroute, Jess Lynch could have been forgiven for focusing inward to recover post-exit. However, Jess chose instead to pay forward the support she received by coaching a new generation of founders. She joined Raiz Capital as Founding Partner, driven by her proclaimed goal to "create the change we want to see in the world." As Jess explained, "We think entrepreneurship is the way to do that. And the more people that can be successful entrepreneurs, the better off we all will be."

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Jess does not just talk about the importance of community - she backs it up through tangible efforts to lift other entrepreneurs. This reflects Jess benefitting firsthand from the cycles of contribution within networks like Boston's tight-knit startup ecosystem. During Wishroute's darkest days, Jess leaned hard on her mentors and investors for backing, including through an emergency crowdfunding round. Now, amidst the "constant storms" of her own journey, Jess makes time to provide that very same support to founders following in her footsteps. As Jess noted, "Your startup journey isn’t just about you or your company - it’s a chance to change the world for the better." By paying forward guidance and insight to struggling entrepreneurs, Jess seizes that chance to positively impact global innovation. Other founders can similarly look to sponsor emerging talent, creating a rising tide that lifts all ships.

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The key insight: Your startup journey isn’t just about you or your company - it’s a chance to change the world for the better. Find ways, big and small, to lift up those still fighting their way along the path behind you.

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The road of entrepreneurship is paved with tribulations. But with Jess’s blend of grit, agility, connection, and compassion, you can turn those stumbling blocks into stepping stones toward success. In this episode of Forward Obsessed, Jess covered many more founder lessons beyond these five. Check out the full discussion if you crave more startup knowledge straight from the crucible.

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