Starting a company asks everything of you. This is a resource for navigating what happens when it doesn’t go the way you planned.
Starting, building, and scaling a company is an existential happening. It asks everything of you: your identity, your relationships, your sense of self-worth. And when things don’t go the way you planned, the experience can feel isolating in ways that are hard to put into words.
What we rarely talk about openly is the pressure and the pain of it: the weight of responsibility to your team, the questions you carry about what investors will think, the grief that can quietly set in when you’ve had to close the doors. The voices that ask, Am I enough? Did I do enough? What does this say about me?
Here’s what we know: you are not alone in this. Others have walked this path — and talked honestly about it — so that you don’t have to carry it in silence.
We’ve curated this collection of our most intimate podcast conversations, essays, and journal prompts to be a companion for wherever you are right now: staring down a short runway, deciding when to close down the business, navigating the aftermath, or simply trying to understand what it means to lead through loss. Start where you are. There’s no wrong door in.
“A company that fails doesn’t mean you are a failure. In fact, it’s an opening and opportunity to find something new within you and for you.”
Ali Schultz
Each of these conversations lifts up a different facet of failure from the leader’s perspective — from facing down a short runway, to deciding when to close the business, to handing over the keys and wondering: what’s next for me, as a leader, now? Browse by theme, or start wherever you feel called.
For when you can feel the make-or-break of this moment.
The “failing process is pressure-packed and painful,” notes Harvard Business School professor Tom Eisenmann. In this conversation with Jerry, he dives into the patterns that contribute to startup failures — and why the familiar advice to “fail fast” often leads founders to false starts, risking capital and time on the wrong solutions. They also explore the pressure founders feel to grow rapidly, the lionization of venture capital, and the true human cost when things don’t work out.
As CEO of a young startup with 6 months of runway, Nigel Sharp finds himself in one of those very moments — feeling the energy of a promising product and the reality of a tightening timeline. How do you balance the excitement and the challenges? How do you discuss the reality of your finances with your team? How do you name your fears — not only of failure, but of success?
Most startups fail. We all know this as much as we try to forget it. The hardest question an entrepreneur can ask themselves is: When do you know it’s over? Derek Bereit, CEO and co-founder of Symptomly, is staring down the end of his runway and wrestling with this very question in real time.
Startups are founded with an outcome in mind. Holding our desired endings builds the drive for our best work. But when things don’t unfold along the lines we desire, it’s easy to generalize the entirety of our efforts as a failure. Tarikh Korula has founded a number of companies but has yet to achieve an exit. Jerry and Tarikh discuss how we define failure — and how we hold the tragic gap, the space between where we do the work and our often elusive aspirations.
For when you’re in the thick of shutting down, or sitting in the quiet after.
Feelings of isolation and loneliness have been well documented amongst today’s leaders. That’s why the simple question “Are you okay?” — asked with genuine concern — can have such a profound impact. At the time of this recording, Avni Patel Thompson was in the wake of shuttering her company, Poppy. Jerry’s open and honest question revealed a well of unprocessed emotions and kick-started the inquiry into her next steps. Avni reflects that while Poppy no longer exists, the mission and purpose that drove it lives on — and that the collapse of her previous business has driven her into greater alignment with her life’s work.
We hear it all the time: failure is good. But we rarely hear about the pain, the shame, and the second-guessing. And even rarer still — what opportunities might lie for our own growth in something ending. Nicholas Russell joined Jerry on the very day he handed over the keys and closed up shop on his startup of 3+ years. In this conversation, they talk about what he’s experiencing now, what he learned, what he wishes he’d done differently, and a surprising path forward.
Matt Tara is the CEO of an e-commerce fashion company that failed but is still very much alive in his head. When the road turned rocky, Matt was forced to put his company to rest — and was left with grief, a felt sense of abandonment, and the understanding of what it means when an entrepreneur says “this is hard.” Most of all, he felt alone, at a loss for peers who could really listen.
How do you know when it’s time? What does it take to come to that realization as the entrepreneur behind the wheel? Ali and Jerry dive into these questions and touch on the perils of scaling and growth without a drive for profitability.
For when the hardest voice you’re navigating is your own.
As many leaders can attest, the harshest critics we face often come from within. Even when we feel confident in our work and abilities, thoughts like Am I doing enough? arise. Once the inner critic emerges, questions of guilt begin to creep in. The challenge is discerning not only what triggers this internal voice, but recognizing what it — the Loyal Soldier — serves to protect.
Ben Rubin comes to Jerry wondering how to better deal with negative inner dialogue. They quickly discover that the inner voice — and more specifically, the feelings that precede it — is a powerful indicator of underlying fear. What opportunities exist in exploring that fear rather than running from it?
We’re often in — or feel that we’re in — uncharted waters, where making things up as we go is a necessity. Feeling lost in those places can be anxiety-inducing. We feel incompetent. Shameful. Like everyone else has figured it out but us. Sharon Salzberg and Jerry explore how owning our anxiety in these areas can actually help us step more fully into our authentic selves.
There’s something calming about finding a target for our blame. In a rough sea of chaos and uncertainty, assigning fault to a person or a moment feels like an unsinkable lifeboat to grasp. We do this as individuals, in organizations, and as a society. But what incredibly valuable opportunities lie in resisting that urge — and what might we learn in exploring a bit more?
For when the dust is settling and you’re finding your footing.
Jerry and Jeremy Bloom illuminate the striking parallels between the pressures elite athletes face and the everyday stressors entrepreneurs endure. They contemplate the inertia that arises from failure and consider the perils of allowing our self-worth to be defined by the attainment of our goals. Jeremy shares why the hardest aspect of leadership is managing your own psychology — and why honing the ability to differentiate signal from noise is paramount.
After an explosive season of personal successes, professional ultramarathon runner Dylan Bowman shares how an abrupt series of injuries and setbacks rattled his perceptions of control and precipitated questions about identity and self-worth. Jerry emphasizes the power of wounds and implores Dylan to allow this period of pain to broaden his capacity to extend compassion to others — and to himself .
Retrospectives play a crucial role in building resilient teams. As organizations face constant change and uncertainty, having a regular ritual of collective learning provides stability and groundedness. Andy walks through a simple framework — What? So What? Now What? — useful in both successes and failures, to discover what’s actually happening, what patterns are emerging, and what next best actions to take.
For many leaders, the experience of rejection hits close to home — it can feel like a dismissal of our very soul. Our initial response may be to thicken our skin, to build a wall behind which we suppress our sadness and our tender selves. But another opportunity exists: one of compassion and strength. The opportunity to meet rejection as a warrior.
As you walk the entrepreneurial path, how you hold what’s happening matters as much as what’s happening. Jerry writes in Reboot: Leadership and the Art of Growing Up about the difference between true grit and false grit — and it’s worth sitting with.
False Grit: False grit is brittle. It’s the sense we are nothing if we can’t take a punch. It feeds a stubbornness that, in turn, can feed delusion, the tendency to tell ourselves that our companies will succeed if only we double down on our old patterns, grip the steering wheel until our knuckles whiten, and bear down. Stubbornness is not the hallmark of the warrior.
True Grit: True grit is kind. True grit persists not in holding on to false beliefs against all evidence, but in believing in one’s inherent lovability and worthiness. It acknowledges the potential of failure, embraces the fear of disappointment, and rallies the team to reach and try, regardless of the potential loss. True grit, the capacity to stick with something to the end, stems from knowing oneself well enough to be able to forgive oneself.
Where might you be exercising false grit? What does this moment call for instead?
“The point of roller coasters isn’t to be better at riding roller coasters; it’s to learn how not to board the roller coaster at all. Resilience isn’t the goal; it’s the path. The goal is the equanimity of a warrior.”
Jerry Colonna
As you listen to each episode and move through this material, keep a journal nearby. Capture what stands out. What you heard — or needed to hear — at this time. What resonates, what hits home, what helps you see things differently.
These questions may serve as useful starting points:
Who are you without your company? How do you separate yourself from your work?
What do you know about yourself? Who are you on your best day — and how are you when you’re at your worst?
What happens when you’re under stress? How do you work with your shadow and blind spots?
What did your family teach you about work and money? What parts of that are you bringing into this chapter?
What fears might be driving this endeavor for you — even now, even in the ending?
Where might you be exercising false grit? Where does this moment call for something truer?
Who can you turn to that you trust completely? What additional support might you need right now?
What’s at the heart of what you’re driven toward? What is the love that pulls you? What brings you joy and moves you forward into what’s next?
On patterns, false grit, and what it takes to stand as a single warrior amid a community of brokenhearted fellow leaders.
Tending to our grief is good human being housekeeping. What's at the heart of what you're driven toward? What is the love that pulls you?
Wondering What's Next? Start With Endings.
Honoring our endings allows us to reflect on how we've grown, brings awareness to the ways we are developing, and supports us in connecting to what lies ahead. The most generative way forward involves a counterintuitive first step: pausing to fully recognize the endings that have taken place.
From Heartbreak, Through Resilience, To Equanimity
There's heartbreak and grief to sit with — and the heart muscle of resilience grows bigger to hold it all, so that we can be at peace in a new place with what we've been through and where we find ourselves.
Sometimes, until we hit a rock bottom, the long string of unfortunate events feels easy to blip over in pursuit of other things. This essay explores what it means when the techniques that used to carry us through stop working — and what that demands of us.
Failing to wait and listen for the sound of the genuine in ourselves keeps us holding an unlived life. When did you start listening to your own heart? What does that look like for you?
Leading in Times of Volatility
How curiosity, compassion, and creativity help us lead amidst choppy market conditions.
The 6 Challenges of Leadership for CXOs
Thinking about the challenges of leadership through six concepts rather than one big hairy challenge can be quite clarifying.
Coaching exists for exactly these moments, the ones where the path forward isn’t clear, the inner critic is loud, and the questions feel bigger than the answers. Reboot coaches have walked alongside hundreds of founders through the full arc of the entrepreneurial journey, including its hardest chapters.
If something here is resonating and you want to explore what support could look like, we’d love to talk. An exploratory call is a good place to start.
