The Leaders We Work With

For more than a decade, Reboot has coached founders, CEOs, investors, and senior teams at the moments that tested them most.

Across many years, Reboot coaching has been present at meaningful inflection points in the lives of founders, CEOs, investors, and senior leaders whose companies and institutions went on to achieve significant public, financial, cultural, and organizational outcomes.

Public-market access: Reboot has supported leaders through the transition from founder-led company to public-market accountability, helping them navigate the identity, relational, and organizational demands that accompany scale.

Successful exits: Reboot has supported founders and CEOs as they navigated not only the mechanics of exit, but the deeper questions of identity, stewardship, responsibility, and what it means to finish well.

Capital formation and institutional growth: Coaching can strengthen the leadership conditions that support investor trust: clearer communication, steadier judgment, stronger relationships, better conflict tolerance, and greater self-awareness under pressure.

Founder-to-CEO maturation: A recurring outcome of deep coaching is the founder’s shift from being the center of gravity to becoming a steward of a larger system.

Executive-team alignment: Reboot’s work often helps leadership teams build the trust, directness, and shared responsibility necessary to lead through complexity.

Crisis navigation: At moments when fear narrows a leader’s field of vision, coaching can help restore perspective, responsibility, and choice.

Human sustainability: The measure of leadership is not only what gets built, but what happens to the human being doing the building.

Finishing well: Coaching can help leaders finish well: to exit with dignity, transfer power with care, and make meaning of what they have built.

The leaders who build, scale, sell, steward, repair, and transform important organizations face psychological and relational challenges that conventional business advice often cannot reach. Reboot works at that level.

Dan Putt

“Coaching offers a unique approach to personal development. It goes beyond simply providing answers or strategies. Instead, it empowers individuals to better understand themselves, their values, and what truly matters to them. Commitment to this self-inquiry is the vehicle for lasting and impactful change. Tactical and strategic changes often work quickly but fade. But changing from the inside out leads to lifelong shifts in who we are and how we show up in the world. When we look within, we give ourselves an opportunity to grow into the type of leader (and human) we aspire to be.”

Dan Putt, Reboot Co-Founder

For more than a decade, Reboot has coached founders, CEOs, investors, and senior teams through some of the most consequential moments in their organizational life: IPOs, acquisitions, succession, rapid growth, board conflict, senior team repair, and founder transition. We know that leadership capacity matters when the stakes are highest. Our work is to help leaders meet those moments with clarity, courage, responsibility, and humanity.

The companies we work with may be known for their IPOs, acquisitions, valuations, products, or cultural influence. But inside every company story is a human story: a founder learning to let go, a CEO carrying fear, a team avoiding the conversation that matters most, a leader wondering who they are without the thing they built. Reboot works there–at the intersection of ambition, power, relationship and meaning.

Reboot’s coaching has been present at meaningful inflection points for leaders and companies that have gone on to raise significant capital, enter the public markets, complete major acquisitions, scale executive teams, manage succession, and build enduring institutions. Our work focuses on the inner and relational capacity required to lead through those moments.

We have seen again and again that the leader’s inner life affects the outer life of the organization. When leaders become more honest, less reactive, more relational, and more capable of holding complexity, better decisions become possible. That is where coaching creates value.

Coaching helps create the human conditions under which responsible leadership becomes more possible.

What follows are portraits from that work. Coaching cannot be credited as the cause of these outcomes. What we can say is that these leaders did real developmental work at moments when the stakes were highest — and that the work was visible in how they led.

THE WORK

These are examples of the leaders we work with, grouped by what they were carrying. Some are in the middle of it. Some are on the other side.

If you recognize yourself in any of this, you do not have to carry it alone. Talk to a Coach

WHAT ARE YOU NAVIGATING RIGHT NOW?

The founder who scaled from mission to public company

The founder of a mission-driven education company grew from early-stage scale into a multi-billion-dollar public company while doing deep work on leadership, culture, delegation, and identity.

A founder began the work as the company was still small enough that culture, product, hiring, and identity were all wrapped tightly around him. Over time, the company became a public company with global reach.

The work was not simply about how to scale an organization. It was about how a founder metabolizes the psychological shock of scale: the loss of intimacy, the need to trust leaders, the fear of becoming performative, and the responsibility of carrying a mission in public. The leader had to keep growing as the company grew, learning not only how to lead more people, but how to remain grounded while the external world began projecting more and more onto him.

The founder who became the public-company CEO without losing the developer’s soul

The technical founder scaled a communications infrastructure company from under 100 employees to a successful public company, navigating the founder-to-public-CEO passage.

A technical founder built a developer-focused company from startup scale into the public markets. The company’s success required him to move from maker to executive, from product storyteller to public-company leader, and from founder-led intensity to institutional discipline.

The work centered on the emotional and intellectual transition from “I understand the product better than anyone” to “I must build a company that can keep growing beyond my direct control.” That meant working with ambition, doubt, board dynamics, team trust, and the loneliness of being the person onto whom everyone projected certainty.

The marketplace CEO carrying mission into the public markets

CEO of a values-driven marketplace helped guide the company through IPO while carrying the tension between mission, community, and public-market expectations.

A values-driven marketplace leader helped bring a beloved community-centered company into the public markets. The company had a powerful identity and a deeply attached community, and going public intensified the tension between mission, growth, investor expectations, and founder mythology.

The coaching work lived in the pressure of that paradox. How does a leader honor a company’s soul while facing the discipline and distortion of the public markets? How does one make hard decisions without becoming hardened? How does one lead through critique from both Wall Street and the original community?

The co-founders who had to grow up faster than the category they helped create

Co-founders of a pioneering podcast company navigated intense founder conflict and role evolution through a successful strategic acquisition.

Two media co-founders built one of the defining companies in the early podcasting wave. The company grew quickly, became culturally important, and eventually sold in a landmark acquisition. Along the way, the founders had to navigate role clarity, conflict, ambition, creative identity, and the emotional reality of building something in public.

The story here is not merely the exit. The deeper story is co-founder development under pressure: two people learning how to tell the truth, fight cleanly, stay in relationship, and make decisions while the company and the category were growing faster than their partnership’s original operating system.

The investor who turned a family-office-style effort into an institutional climate platform

Climate investor grew a sub-scale sustainable-investing platform into a multi-billion-dollar institutional firm while deepening his conviction, voice, and leadership capacity.

An investor began with a comparatively small, thesis-driven sustainable-investing effort and built it into a multi-billion-dollar institutional platform focused on the climate transition.

The work was about more than AUM growth. It was about conviction, voice, authority, and stewardship. He had to keep trusting a thesis before the world fully caught up to it, then learn to carry success without losing the clarity that made the strategy distinct in the first place.

The entertainment executive who finished well

A long-tenured music industry CEO/chairman completed a major executive chapter and retired well after more than three decades in the industry.

A senior music industry executive came to the end of a long and successful career and faced a deceptively difficult leadership passage: not how to win more, but how to finish with dignity, grace, and love.

The work was about letting go without collapsing, retiring without disappearing, and honoring the people and institution he had served. He was able to leave not in bitterness, grasping, or denial, but with clarity, gratitude, and a sense that the job had been completed.

The consumer founder who built, sold, and then had to ask what success was for

Founder of a mission-driven consumer brand scaled to major commercial success, sold the business, and worked through the identity transition beyond the company.

A consumer-products founder built a mission-driven brand that became widely recognized, scaled into a major business, and was eventually acquired. On paper, this is the clean founder success story: build the brand, grow the company, sell the business.

But the more useful Reboot story is what happens inside the founder along the way. The work involved ambition, control, mission, pressure, and the deeper question of who one becomes after the company no longer needs to be carried in the same way. The sale was not the end of the story. It was the doorway into a new question: what now, and who am I when I am no longer proving this company into existence?

The film-company leader learning to hold cultural success without being swallowed by it

Co-founder of an independent film studio navigated the emotional and strategic demands of cultural prominence, commercial success, and institutional scale.

A co-founder of a fiercely independent film company helped build one of the most culturally important studios of the last decade. The company went from outsider brand to awards powerhouse, while trying to preserve its creative edge and identity.

The developmental work here is the passage from insurgent to institution. How does a leader remain artist-centered as the stakes rise? How does one keep making brave decisions when success brings more money, more attention, and more expectation? How does a creative company grow without becoming the kind of company it was created in opposition to?

The sports owner whose leadership helped turn an under-loved franchise into a championship institution

Owner/philanthropic leader helped elevate a women’s sports franchise into a championship team and cultural institution while deepening public leadership and community impact.

A sports and philanthropic leader helped steward a women’s professional sports franchise into a new era of recognition, investment, and championship success.

The story is not just the title. It is the leadership stance behind it: taking women’s sports seriously before the market fully caught up, investing in infrastructure, insisting on excellence, and linking team success with community, justice, and cultural meaning. The work involves power, visibility, stewardship, and the discipline of using capital and platform in alignment with values.

The founder who left the old platform and built a life more aligned with his practice

Public media leader separated from a legacy institution and later from a co-founded company, then built a more aligned independent media and teaching platform.

A media personality and entrepreneur moved through a complicated separation from a long-standing institutional identity and from a business partnership that no longer fit. He had built a public life around mindfulness, but the harder work was living the teachings in the middle of conflict, transition, and reinvention.

The achievement was not simply launching the next podcast or newsletter. It was becoming happier, freer, and more aligned. The coaching arc was about telling the truth, grieving what was ending, separating without becoming cruel, and building the next chapter from practice rather than performance.

The direct-to-consumer founder who scaled a beloved brand into the public markets

Founder of a mission-linked consumer brand scaled the company to a multi-billion-dollar public listing while working through the founder-to-institutional-leader transition.

A consumer founder helped build a category-defining brand with both commercial and social-impact dimensions. The company grew from startup energy into a public-company environment, carrying the tension between brand, mission, retail operations, growth expectations, and leadership maturity.

The Reboot story is the inner passage beneath the business milestone: moving from charismatic founder/operator to institutional leader, learning how to share power, absorb criticism, and keep the company’s values real as scale increased.

The fintech founder navigating the whiplash of extraordinary valuation and market repricing

The fintech founder navigated hypergrowth, major valuation milestones, a failed acquisition path, market repricing, and continued company-building without letting external valuation become identity.

A fintech founder led a company through enormous external validation, including a multibillion-dollar valuation, followed by the harsher reality of market repricing and delayed liquidity.

This is a strong story because it is not just a triumphal fundraising narrative. It is about staying grounded when the outside world first overvalues and then undervalues you. The developmental work is about self-trust, resilience, judgment, and the ability to keep leading when the story the market tells about you changes faster than the company’s actual work.

The consumer founder who helped make mission-driven retail public-company real

The co-founder of a mission-driven consumer brand scaled from startup to public company while navigating the founder-to-institutional-leader transition.

A consumer founder helped build a company that changed the way people bought a basic product and then carried that company into the public markets. The company began as a sharp, mission-driven challenger brand and became a public company with national recognition.

The work underneath the business story was about holding mission, brand, scale, and co-founder leadership at the same time. He had to learn how to keep a company’s original moral and cultural clarity alive while the organization became larger, more complex, and more visible. The developmental question was not simply “How do we grow?” but “How do we grow without becoming hollow?”

The fintech founder whose company became infrastructure for an entire ecosystem

The fintech founder scaled an infrastructure company to category-defining status while navigating valuation swings, regulatory pressure, liquidity complexity, and the emotional cost of being a symbol for an entire sector.

A fintech founder helped build a company that became core infrastructure for a generation of financial technology products. At its peak, the company reached a multibillion-dollar valuation and became one of the most important private companies in its category.

The public story includes funding, valuation, regulatory pressure, and a famously complicated path around acquisition and liquidity. The Reboot story is the internal one: how a leader stays steady when the market first anoints you, then questions you, then revalues you. The work was about learning not to outsource identity to valuation, press, investors, or regulatory uncertainty.

The founder who built a people-operations company and endured the long road to liquidity

The founder of a major HR/payroll platform scaled the company, prepared for the public markets, and continued leading through delayed liquidity and market uncertainty.

A founder built a company designed to help small businesses handle the messy human and administrative side of employment. The business grew substantially, raised significant capital, and prepared for the public markets, only to have timing, market conditions, and the realities of being a private company complicate the expected path.

This is a useful story because it is not the clean mythology of “build, IPO, win.” It is about persistence, patience, and the founder’s capacity to keep leading through liminal space. The company became real and meaningful long before the market provided a neat ending. The work was about staying in relationship to purpose when the external milestone kept moving.

The investor who named a category and then had to keep earning her own voice

Seed investor built an enduring venture firm and public investment voice after shaping one of the defining concepts in modern venture capital.

A venture investor helped shape the language of the startup world by popularizing a term that became central to how the industry talks about billion-dollar private companies. She then built a seed-stage firm with a distinct point of view around consumer behavior, enterprise transformation, and the future of work and life.

The inner arc is about claiming voice. It is one thing to be known for a phrase. It is another to keep building a body of work, a firm, a public thesis, and a leadership identity over time. The work here is about authority without mimicry: trusting one’s pattern recognition, staying close to one’s own way of seeing, and letting the firm become an expression of that seeing.

The investor who built a consumer venture firm around taste, judgment, and conviction

Founder of a consumer-focused venture firm grew the platform to nearly $3B AUM while developing a clear public voice, investment thesis, and institutional presence.

A venture investor built a firm around a differentiated understanding of consumers, culture, commerce, and behavior. Over time, the firm grew into a multi-billion-dollar platform and backed companies that helped define modern consumer technology.

The developmental work is about conviction in a pattern before the market fully validates it. It is also about being a woman building authority in an industry that often rewards a narrower, louder, more performative version of confidence. The deeper story is not only fund growth. It is the maturation of taste into thesis, and thesis into institution.

The designer-founder who helped build a global company and then had to find the next act

Co-founder of a global marketplace helped build the company into a public-market giant, then began the deeper work of identity, service, design, and next-chapter leadership.

A designer-founder helped create one of the most important consumer technology companies of the last twenty years. The company survived near-death, became a global platform, and entered the public markets at extraordinary scale.

But after that kind of success, the real question changes. It is no longer “Can I build?” but “Who am I after building this?” The developmental story is about moving from founder identity into generative next chapters: design, housing, philanthropy, public service, new ventures, and the search for usefulness beyond the original company.

The founder-CEO who did not set out to become the archetypal CEO

The technical founder scaled a global commerce platform from startup to public-company giant while integrating maker identity with CEO responsibility.

A technical founder built one of the defining software companies of the modern internet economy. The company began as a tool for his own need and became a global commerce platform used by merchants around the world.

The developmental arc is the reluctant CEO becoming the actual CEO. He had to learn how to lead at a scale that no one could have imagined at the beginning, without abandoning the maker’s intelligence that made the company possible. The work was about holding technical conviction, culture, product judgment, and public-company responsibility without surrendering to the caricature of what a CEO is supposed to be.

The founders who chose mission protection over the obvious venture-capital script

Founders of a creative platform chose public-benefit governance to preserve mission and resist pressure to optimize only for shareholder return.

A group of founders built one of the most important creative platforms on the internet and then made a structural choice to protect the company’s mission by becoming a public benefit corporation.

The public milestone is unusual because it is not a conventional exit or IPO. It is a governance choice. The deeper leadership passage is about resisting the default script of growth, liquidity, and maximization when those goals threaten the company’s soul. The work sits in the tension between ambition and stewardship: how to build something influential without letting influence become extraction.

The mental-health founder who helped merge care, technology, and scale

The founder of a digital mental-health company scaled the business into a major merger, helping create one of the leading platforms in the category.

A founder helped build a mental-health technology company at a time when the need for accessible care was becoming impossible to ignore. The company eventually merged with another major player to create a large, integrated mental-health and wellbeing platform.

The business story is about category formation, scale, and strategic combination. The human story is about carrying a mission in a field where the stakes are not abstract. The leader had to work with urgency without becoming consumed by it, and with ambition without letting the company’s growth outrun the care at the center of the work.

The consumer founder whose blocked exit became a different kind of leadership test

The consumer founder built a major brand, navigated a blocked billion-dollar acquisition, and continued leading the company through the emotional and strategic reset that followed.

A consumer founder built a disruptive personal-care brand that became valuable enough to attract a major acquisition offer. The deal was blocked by regulators, forcing the company to continue forward independently after what had looked like a defining exit.

This is a powerful story because the developmental passage is not only through success but through interrupted success. The work is about what happens when the finish line disappears. The founder had to metabolize disappointment, reassemble conviction, and keep leading employees, investors, and customers after the story changed in public.

The venture builder who kept experimenting with the model

Venture investor and firm founder evolved from successful investor into ecosystem builder, experimenting with new models of founder support, community capital, and venture partnership.

A venture investor built and spun out a firm, backed important companies, and continued experimenting with new structures for supporting founders and startup communities. Rather than simply becoming a conventional senior investor, he kept asking what venture capital could become if it were more founder-centered, networked, and community-rooted.

The developmental story is about authority and reinvention. After years of success, the temptation is to defend the model that made you known. His arc is more interesting: keep building, keep experimenting, keep creating vehicles that support others. The work is about eldering in venture without calcifying.

The founder who moved from public identity into quieter moral clarity

The founder of a beloved internet platform moved through the identity transition from public founder to more grounded, self-authored next chapter.

A public-facing founder built a beloved company and became associated with a particular kind of humane, creative, internet-era optimism. Over time, the harder work became less about company-building and more about finding a life and leadership stance after public founder identity.

The coaching story is about metabolizing visibility. How does a leader separate their own worth from the thing they built? How do they carry public admiration, criticism, confusion, and projection without losing access to their own inner life? The outcome is not just another company. It is a more grounded relationship to self, work, and public meaning.

The investor moving from deal success to firm stewardship

Senior venture investor shifted from individual dealmaker success toward broader firm leadership, succession, culture, and stewardship.

A venture investor with a long record of company-building and founder support moved through the passage from individual investor identity to broader firm stewardship. The question was no longer simply “What deals do I believe in?” but “What kind of firm, culture, and next generation am I helping build?”

The work involved voice, succession, authority, generosity, and the move from proving oneself through wins to transmitting judgment to others. In venture, this passage is easy to avoid because the next fund, next deal, and next markup can always distract from the deeper question. But the work of elder leadership is different: build the container, not just the portfolio.

The founder whose company grew up around a simple but radical promise

Founder scaled an employment infrastructure company that helped small businesses support their teams, while growing from operator-founder into institutional leader.

A founder built a company around making it easier for small businesses to take care of their people. The company’s promise was practical, but beneath the product sat a moral idea: employment should not be so administratively punishing that only large companies can do it well.

The developmental arc was about turning a founder’s practical insight into an enduring organization. That required hiring leaders, trusting teams, living through market cycles, and staying connected to the human purpose inside a highly operational business. The success was not only revenue, funding, or scale. It was building a company that made other companies more humane and more functional.

These are examples of the leaders we work with, grouped by what they were carrying. Some are in the middle of it. Some are on the other side.

If you recognize yourself in any of this, you do not have to carry it alone.

TALK TO A COACH

The Leaders We Work With

For more than a decade, Reboot has coached founders, CEOs, investors, and senior teams at the moments that tested them most.

THE WORK

These are examples of the leaders we work with, grouped by what they were carrying. Some are in the middle of it. Some are on the other side.

If you recognize yourself in any of this, you do not have to carry it alone. Talk to a Coach

WHAT ARE YOU NAVIGATING RIGHT NOW?

Extras #23 – Unleashing Potential: Insights on Leadership, Self-Discovery, & Overcoming Fear – with Noah Kagan

#177 – What Does It Mean To End Well? – with Randy Goodman

How I Built a 50M/Year Company: Frameworks & Reflections

These are examples of the leaders we work with, grouped by what they were carrying. Some are in the middle of it. Some are on the other side.

If you recognize yourself in any of this, you do not have to carry it alone.