It seems against all odds and unlikely that this has been my journey. Eleven disruptive companies that all faced existential crises. Seven became unicorns. Three filed for IPO. Three were acquired. Together, they exceeded $400 billion in peak cumulative valuation. My journey sounds unbelievable. And that’s fair—it is highly improbable.

Note: the links below are to pages where I’ve written more extensively on the highlighted topics.

Or, you can begin with the Talent Whisperers Pages. There are many pages of lessons and observations from my journey, reading, conversation with other leaders and enagement with customers leading to many concepts and areas to explore.

The Against All Odds Track Record That Invites Skepticism

I’ve lived and led through it in pivotal roles. But it also wasn’t a solo journey against all odds.

This path was forged with extraordinary people—determined founders with bold visions, engineers with commitment to their craft and the mission, and teams willing to operate at the Edge of Chaos, where the outcome is uncertain, but opportunity abundant. These were the kinds of people who cultivated Learned Resilience through deliberate practice and demanding experiences. They all had a mission and purpose they were passionate enough to fight for. They were open to adopting (or evolving) rituals akin to those captured in Weathering Storms. These teams were willing to live with tension, ambiguity, and urgency, without tipping into panic.

But Did That Really Happen?

It did. And not because there’s a single, simple formula or secret.

The rituals that helped us survive and thrive were never mine alone, and they were never static. They emerged through collaboration—refined in the heat of each company’s unique challenges. What made them possible was finding and building teams with the right kind of people. These were people willing to live at the Edge of Chaos, open to evolving together, and grounded in Learned Resilience. The work was always collective, always adaptive, and always real. One recruiter put it this way: “You have a knack for picking the right companies—and the right kinds of people.”

It’s not just about the role I played. The focus is on the ability to recognize founders and employees…. This ability also involves creating environments that foster thriving at the edge, not shrinking from it.

So yes, it’s rare. And yes, it still surprises me at times.

But when people ask, “How is that even possible?” I offer this:

  • Well … it did happen.
  • There is no single or simple reason.
  • I have an affinity for finding founders and teams passionate about making it happen.
  • Even when many things are done right, success still demands hard work and is never guaranteed.

Moments That Defined this Against All Odds Journey

Maybe it wasn’t just luck. Maybe I had an early start in seeing and defining what makes software teams thrive.

In my very first job, I helped create the world’s first Integrated Software Development Environment. We were solving real problems that slowed down engineers—helping them become more efficient, more consistent, and more capable of building complex, reliable and extensible systems. It wasn’t a stand-alone system; it operated within heterogeneous computing environments, supporting multiple languages and methodologies. That experience shaped everything that came after. It was the birth of a passion for understanding every aspect of what makes software development teams and companies successful.

All 11 of the companies I’ve worked with have been, at their core, software companies. That matters. It started as a technical role of understanding how software systems worked and how people could use them most effectively. These companies were all trying to be disruptive within their own space, and hence each one on its own was already operating against all odds. It grew into a passion for recognizing the people, patterns, and rituals that enable technology teams collectively not just to build—but to survive, adapt, and thrive. I now also see both positive and negative patterns reflected in today’s AI-generated systems and code.

This has helped in recognizing missions, environments and leaders with the potential to succeed. It’s not magic. It’s pattern recognition born from decades of watching and incrementally discovering, adjusting, and improving what works best (and who works best) on challenges under pressure, and who grows stronger when others give up.

A Varied Journey

At BroadVision, we barely made payroll before becoming a rocket ship that reached a $26B valuation just five years later. While at IMVU, we helped codify what would later become known as Lean Startup. At Intuit, I formed and lead a team that created the foundation for what became QuickBooks Online. Later at Twitch, we rapidly scaled engineering in the chaos of breakout growth while continuously improving reliability and scalability.

At Prosper and Hum Capital, I’ve seen how rituals, trust, and data can redefine how capital flows. Earlier at Softlab, we bet completely on proprietary hardware that went end-of-life. That could have spelled death for the company, but I re-architected the operating system to run on newer hardware. This included building an HTML browser and WYSIWYG editor years before the internet took off. Then as part of a three-person team, we re-architected it again to run on commodity PCs and Unix services through UDP/IP internet protocols anchored on a proprietary, distributed OODBMS.

Often, it was the near-death moments that forged our Learned Resilience and shaped us most.

Not every company I joined became a unicorn, but nearly all faced moments when survival was uncertain. The difference lay in founders unwilling to give up under extreme stress and adversity. It also depended on a collective capacity for Learned Resilience, which is a combination of mindset, ritual, and adaptive response—not individual heroics.

Testimonial: A Steady Hand Behind Extraordinary Journeys

From a former colleague over the last years:

“Chris Dolezalek doesn’t chase headlines. He builds what endures—often in moments when everything seems on the line.

“He’s helped shape 11 companies that beat steep odds to survive. But the numbers are never what defined his work. It’s the people. The teams that stuck together when it would’ve been easier to quit. The quiet wins behind the scenes. The moments when leadership meant listening and adjusting, not rigidly dictating.“

What My Journey Taught Me: Why So Many Wins in a Game Built on Failure?

I have learned how to spot, build, and grow the necessary Learned Resilience in others. That higher level of resilience, perseverance and grit is needed when operating against all odds at the edge of chaos.

1. I’ve Cultivated Learned Resilience Myself.

Through sports leading to winning nationals and competing at world championships, business, and hard-earned lessons, I developed the mindset that there is always a path forward—not blindly, but intelligently and creatively. I don’t see obstacles as stop signs. Instead, I see them as invitations to find a better route.

2. I’ve Learned to Choose Resilient Founders and Teams.

Over time, I began to recognize certain patterns: which founders operate well at the Edge of Chaos? Which leaders actually thrive there, not just survive? I learned to choose companies with gritty cultures, people who could navigate turbulence with clarity and courage.

3. I’ve Learned to Hire for Learned Resilience.

When building or joining teams, I look for people who love challenges, take pride in their craft, are open-minded and lift everyone around them. People who pursue achievable, meaningful challenges with energy. Those who fail and grow. Who learn and reset in patterns that compound. I’ve continuously refined the methods for hiring the best. And equally important, onboarding them in ways that foster the right mindset.

4. I’ve Learned to Teach and Support It.

I’ve spent years helping others develop their own resilience. I challenge peers and team members in ways that stretch but don’t snap. I help people learn from their stumbles, understand the systems they operate within, and approach problems with innovation and ownership. Resilience is not merely a trait—it is a teachable practice.

5. Incremental and Continuous Learning through AI and beyond.

I’m a firm believer that continuous digital transformation requires continuous human transformation. We cannot rest solely upon lessons learned from the past in a world changing at an increasing rate. We must move beyond just understanding how to whisper to human talent to understanding AI Whispering.

At home, I’ve started using AI to code a prototype of a virtual senior companion in Android Studio. At work, I’ve started a project using Cursor to extend how we using existing code and financial data on companies to go beyond understanding the financial health and trajectory as a whole to understanding how they are doing in different vectors and segments to discover potential that may have otherwise been overlooked. One of my advising roles is with a founder of a biotech company that is using AI to learn how to predict which molecules and proteins will bind to enhance drug and side-effect discovery. Ultimately, leadership is my sweet-spot and I keep learning on that front, but I do feel it’s important to truly understand the challenges my teams face to best help them excel as well.

And yes, luck matters greatly when playing against all odds

Some of it truly is luck. Being at the right place, at the right time, having come across the right connection. But even then, what we do with luck matters. I’ve seen people squander good fortune—and I’ve watched others turn bad luck into their best learning.
Learned Resilience is how we metabolize both.

It’s never a journey alone

I have never believed that I succeeded so often because I had all the answers. I believe I succeeded and helped those around me succeed because I kept showing up. Because I could recognize and understand systems and environments that held potential but came with challenges where the need for resilience was real. To break new ground and build disruptive products and systems, you need to be comfortable and effective at operating under stress at the edge of chaos. And because I was surrounded by and helped grow teams who knew how to loop through challenge, reflection, and recovery, again and again.

That’s the Learned Resilience Loop—the story behind those eleven companies. Not luck nor brilliance alone. Also, not just choosing the right founders or products. Vibrant through passion and purpose and the ability to hire, inspire, and retain talent. It is the combination of all these, and the persistence to see them through. Nor is it solely about recognizing which processes best suit a situation. But, some of all of these and whatever else is needed to persist through to success. Learned Resilience—cultivated, lived, and shared.

The Companies on a Journey Against All Odds

After Moving to Silicon Valley

  • Cooperative Solutions
    Joined as an early-stage startup. Most funded tech startup in Silicon Valley at that time. Acquired by Bachman Information Systems for undisclosed amount.
    Employed as: Director of Product Development and site director for product BU when acquired by Bachman, Inc
  • Informix, Inc – joined as a mature company. It was acquired by IBM for $1B (equivalent to $1.7B in today’s dollars)
    Employed as: Senior Manager Engineering
  • BroadVision, Inc. – joined as an early-stage startup. Reached profitability before filing for IPO as the second fastest growing company on Nasdaq during dot com. It achieved a $26B valuation (or $47B in 2024 dollars).
    Employed as: VP Engineering responsible for 7 product lines at the fastest growing software company on Nasdaq in the dot-com days

After my sabbatical to Teach K-8

  • Intuit, Inc. – joined mature company. I started as an individual contributor. Led internal startup to build MVP of QuickBooks Online to move Intuit to Web. 2024 Valuation $175B.
    Employed as: Director, Engineering
  • Yahoo – joined as a mature company. Lead world’s largest casual gaming platform. Yahoo’s peak valuation was over $125B.
    Employed as: Head of Engineering for Yahoo!Games Engineering as the biggest social gaming site of the time
  • IMVU (now Together Labs) – joined as a mid-stage startup. Aka “The Lean Startup” Still going and being coached/advised by me. It has raised a total of $77.6 million in funding. The Lean Startup is a methodology for creating and managing startups by using continuous innovation to build products.
    Employed as: Director, Engineering – Improved agile and continuous deployment at the company behind the book “The Lean Startup” and the world’s largest virtual goods catalog.

Twitch and Beyond

  • Twitch – joined as an early-stage startup. Acquired by Amazon. 2024 Valuation $45B.
    Employed as: Exec V.P. Engineering at Rapid growth/paradigm shift in video streaming.
  • Pure Storage – joined as a mid-stage startup Pre-IPO. Filed IPO. 2024 Valuation $16B.
    Employed as: Director Engineer at the fastest growing infrastructure company to date – joined pre “unicorn” IPOing
  • Prosper Marketplace – Served as VPE and CTO at late-stage startup Pre-IPO. Filed for IPO, still pending.
    Changed Rituals that saved the company, As of 2024, Prosper Marketplace has originated over $25 billion in loans.
    Employed as: V.P. Engineering at one of the pioneer Fintech companies using ML and AI to determine personal loan, HELOC and Credit Card credit worthiness to match with investors.
  • Hum Capital – joined as an early-stage startup. Now profitable and still growing.
    Employed as: Exec V.P. R&D Funding platform pairing growth companies with investors through the use of AI and ML to evaluate whether companies’ live and trending financials match investor criteria to democratize access to capital. Acted as interim CPO.

Before Moving to Silicon Valley

  • Kleen-Rite, Corp – First paycheck was as a janitor cleaning floors in federal buildings First “promotion” when my boss discovered I knew how to fix cleaning machines, which resulted in my first promotion. Also did construction work.
  • Kasemir Construction – Built a house from the foundation up – doing carpentry, masonry, flooring, roofing, plumbing, electrical work, etc.
  • Darden Business School (U.Va.) Executive Program – waiter and bartender to pay for school. Got to meet lots of interesting execs from various locations and industries.
  • Atmosphere Sciences Research Center– Acid Rain Data Analyst – Results published in Scientific American and presented to the U.S. Senate.
  • Softlab, GmbH – joined as an early-stage startup. I was architect for the World’s 1st Integrated Software Development Environment, which began my journey of learning what makes software teams succeed. Initial acquisition by BMW was at $300M valuation or $8.2B in today’s dollars.

Looking back, the numbers are easy to count — valuations, rounds raised, teams rebuilt. But what can’t be quantified as easily are the lives touched and the ripples that followed. The true story isn’t just about surviving impossible odds. It’s about what those survivals made possible for others.

Amplifying Lives, Not Ledgers

From early childhood, I was taught that success is measured not by what we accumulate, but by how much we amplify the lives of others. That belief shaped every decision long before the titles, valuations, or crises that later defined my career.

On my journey so far, across eleven companies, I’ve been motivated by purpose not prosperity.

It’s the natural consequence of a philosophy rooted in contribution — and yes, a readiness to seize good luck when it arrives and the resilience to endure when it doesn’t. My measure of success has always been how far that positive impact reaches: in lives changed, teams strengthened, and futures expanded.

The deeper measure of success lies not just in the teams who grew stronger or the employees who prospered, but in the unseen ripples: the small business owners, the creators, the families whose opportunities expanded through the technology we built. Whether through financial empowerment at Intuit, Prosper Marketplace, and Hum Capital; creative joy at Yahoo! Games, IMVU, and Twitch; or the quieter, B2B amplifiers that strengthened other enterprises — Softlab GmbH, Cooperative Solutions, Informix, BroadVision, and Pure Storage — my journey has always been about amplifying the well-being of others, not accumulating what I can’t take with me in the end.

P.S. Why I Write to help others succeed against all odds

This is also why I write about lessons I gathered on my against all odds journey on topics where my pages show up at the top of Google search results and AI prompts all around the world.

Leadership as Stewardship

Each of these reflections carries forward the same core belief: that leadership is a form of stewardship, and that the true return on luck, labor, and learning is the number of lives made fuller by our passage. The companies were just the canvas; the people, the art.

See Also: The Unseen Hand: Deconstructing the Essence of a Talent Whisperer

Visual Footnotes

Books that shaped the journey so far

Many of these also describe other against all odds struggles to learn from. I have consumed many of these more than once as part of my passion to become the best at this. And the list continues to grow. While others may read fiction or fantasy, these are what most awakened my passion. While others listen to music and podcasts, I learned to consume books like these over and over at 4x speed. This allows me to start and finish a book during a one-hour commute.

CDs Books for Leaders to help succeed against all odds

Companies and systems where rituals made impact against all odds

I not only helped companies I worked at, but also companies we worked with. Below are some of the companies where I’ve helped improve the SDLC in various ways include: Softlab GmbH, Cooperative Solutions, Bachman Information Systems, Informix, BroadVision, Intuit, Yahoo, IMVU, Twitch, Amazon, Pure Storage, Prosper Marketplace, Hum Capital, Together Labs, Allianz, American Airlines, Bank of America, BMW, British Airways, Circuit City, Daimler Benz, Deutsche Bank, Deutsche Telekom, Fiat, Grainger, Home Depot, Longs Drugs, Pets.com, Mrs. Fields Cookies, Microsoft, Munich Re, Pets.com, Royal Bank of Scotland, RS Components, Sony and Volkswagen. I was also an architect at the company that built the world’s first Integrated Software Development Environment.

Still Skeptical about the Against All Odds Stories?

Good. You should be. There is no exact science or process to achieve this. There is also always luck involved.

My “Creed”

Recently, a former colleague as me what my calling was – why I chose to do what I do and how I do it. Upon reflection, I came up with this:

Chris' Creed - How CD Chooses to live

This collective continual learning, imho, also includes AI systems. Many say that AI is still years away from achieving continual learning. My belief, based on my experience with AI, is that it has arrived when you consider the larger eco-system that includes the humans that build, interact with and create data for AI. AI brings to us knowledge we never had access to before. With that data and with AI, we can now generate new knowledge, new functionality, and new content. Once released or published, this new content creates and generates new training data. That is a cycle of continual learning which results in how AI operates and what it presents to us is continually evolving.

Some “Against All Odds” stories that I have read at least once throughout my journey to continually inform and remind myself and my teammates of how others may have overcome this or that similar challenge.

See Also – Other Against All Odds Stories.

  • The Everything Store by Brad Stone – A sweeping look at how Jeff Bezos built Amazon through bold bets, high standards, and relentless adaptation.
  • Becoming Steve Jobs by Brent Schlender & Rick Tetzeli – How Jobs evolved from a reckless founder to a deeply reflective leader who inspired extraordinary teams.
  • The Upstarts by Brad Stone – The dramatic rise of Airbnb and Uber—and the mindset of founders who reshaped industries against all odds.
  • Creativity, Inc. by Ed Catmull & Amy Wallace – Inside Pixar’s culture of experimentation, resilience, and the pursuit of creative excellence.
  • Shoe Dog by Phil Knight – A brutally honest memoir about building Nike from the edge of collapse.
  • The Hard Thing About Hard Things by Ben Horowitz – Facing startup near-death moments and making tough calls.
  • The Ride of a Lifetime by Robert Iger – A candid look at how Disney’s longtime CEO led through uncertainty, creativity, and values-driven transformation.
  • Grit by Angela Duckworth – Why perseverance often matters more than talent.
  • The Infinite Game by Simon Sinek – Why playing for long-term resilience matters more than short-term wins.
  • Start With Why by Simon Sinek – Why great leaders inspire action by clarifying purpose.
  • The Phoenix Project by Gene Kim, Kevin Behr, and George Spafford – A novel about IT, DevOps, and overcoming organizational dysfunction.
  • Peak by Anders Ericsson – The science behind world-class achievement.
  • The Slight Edge by Jeff Olson – Small choices that lead to extraordinary success.
  • Thinking in Bets by Annie Duke – Decision-making in high-stakes environments.
  • The Five Invitations by Frank Ostaseski – Lessons on transformation from facing death.
  • Brutally Honest by Emily Chang – Leadership in ruthless, competitive climates.
  • The Culture Code by Daniel Coyle – Transforming groups into high-performing cultures.
  • The Coming Wave by Mustafa Suleyman – Navigating existential tech and global threats.
  • Range by David Epstein – Why generalists win in uncertain, evolving systems.