195: I Wrote a Book

195: I Wrote a Book


How I wrote The Path to Pivot, who it's for (venture-backed founders), why I self-published, and what's next

This week's issue of Cultivating Resilience is brought to you by The Path to Pivot—a playbook for startup founders who want a second chance to swing big.

I wrote a book. It's a really niche one.

If Atomic Habits is a book that pretty much anybody can get into—how to more easily change your behavior and build systems to get closer to the things you want—my book is the exact opposite.

The Path to Pivot is specifically written for venture-backed startup founders who have lost conviction in their company's current strategy and direction. The ideal reader has raised money, is trying to get to a huge outcome, and wants to give themself a second chance to reset their trajectory and pursue an ambitious vision.

→ Announcement post on Twitter / Linkedin

I want to write a lot of books in my life. But writing books take time and a lot of upfront investment.

It's important for authors to write books about topics that not only are they knowledgeable about but that they're perhaps one of the best-positioned people to write about.

That's why I chose this topic. As a three-time startup founder that attempted an unsuccessful pivot in 2012-13 and a more successful pivot in 2018-2019, I have a credible expertise and a bit of a platform about what it takes to make the leap.

That hasn't been the case for all my book ideas.

The Abandoned Book Proposal

I haven't talked a lot about this, but I spent many months in 2021 working on a 50-page book proposal about resilience called Resilience Rules: How we adapt in the face of change and why it matters.

This would be my traditionally published piece.

It featured the four skills of resilience and included a lot of different stories and examples and ways that individuals, leaders, organizations could become more resilient and responsive to change.

I was proud of investing a lot of effort in what is effectively

  • a product pitch
  • a market segment
  • a competitive analysis
  • a go-to-market strategy
  • a book "demo" (detailed table of contents + 2 sample chapters).

The handful of literary agents that I showed it to felt that the material was well-researched, well-organized, well-defined—but ultimately, I didn't have the platform or the unique angle or unique background to make this a remarkable book that could be sold.

The response was a big blow. My motivation to author a book was like a two week old can of Diet Coke. But I couldn't argue with them. I'm not a cancer survivor. I didn't recover from bankruptcy. I wasn't writing about a devastating loss nor did I have a particularly strong connection to resilience at the time. (Part of why I renamed the newsletter was to try and build some of that platform)

In the end, I shelved the proposal and tried not to think about books for a while.

Skipping the Traditional Process

The traditional publishing process has come under fire because it takes so long, there are many gatekeepers, and authors get a very small percentage of the total revenues while being asked to do an increasingly larger share of the publicity.

But still, there is a lot of status and recognition that comes with doing a deal with a Big 5 Publisher (link) or the many smaller presses out there.

I would love to be traditionally published, but chose to self-publish The Path to Pivot. In that way, it joins the ranks of books like The Mom Test, Introspect, and The Pathless Path, all books that skipped the traditional publishing process.

I chose this for several reasons:

  1. I want to get something out into the world sooner
  2. I didn't want to feel beholden to someone else's expectations for what the book needed to be
  3. I wanted to focus on my core audience without feeling the need to expand the market to business readers more broadly
  4. I'd rather have a slow build up than a spike and dropoff (link)

The Process

I'm really proud of this book and it was a winding road to get here.

It started as a series of tweets for the August 2022 Ship 30 and then became a series of essays I published on Medium later that fall. I then wrote an outline and thousands of words of a business fable version of the book in the summer of 2023 that was meant to illustrate the Path to Pivot framework. But halfway through, I got feedback the format wasn't working for early readers and scrapped all of it to make a more practical and tactical playbook.

Even though I've been writing this newsletter for just about 4 years, with 200 issues under my belt, the book was a mot more cognitively demanding.


Because a newsletter can be about a different topic every week. It can have a different format, it doesn't have to reference past things that you've talked about, and it is self-contained.

I had to noodle a lot on the core premise of the book, the major chapters, having case studies that map to the big ideas of the chapter, and the ordering of the chapters. After each round of reader feedback my editorial partner Rhea and I went back and made tweaks small and large to clarify, tighten, and elaborate.

The truth is, I'll probably keep tweaking it right up until I have to submit the text for print distribution. Because I want it to be as good as possible. I'm playing the long game.

Applications Beyond Founders

Here's what I write in the introduction:

This book is written for founders and CEOs of venture-backed startups contemplating—or in the middle of—a major shift in their business.

If that’s not you, that’s cool. Maybe you’re an indie hacker, corporate executive, or angel investor. There is still something here for you, but I would recommend you to tweak the advice as needed.

I’ve taken my own advice and written for a specic niche: the early / mid stage startup funded by VC dollars. My target reader is the person in the arena1, face marred by dust, sweat, and blood, facing a tough decision. This book is for you.

But even though this is not meant to be a fun, cocktail party book a la Gladwell or Pink, there are applications beyond this niche audience. The Inner Game of Tennis has become a bestseller in the "mental strength and coaching for performance" field despite being explicitly about how tennis players can improve their play.

That's because readers understand to consume the material as a metaphor, as context beyond tennis. So if you aren't a founder, there might still be something interesting to draw from the book. But you'll have to extrapolate the lessons for your own context, now that you understand who it is primarily for.

The Hard Sell

If you have gotten value from this free newsletter that I've published nearly every week for the last four years, watched any of my videos, listened to any of my podcast appearances, or offered beta reading for the book: thank you.

I am grateful for your interest and for your gift of attention. And if you'd like to show any gratitude to me and my work, getting this book and leaving a positive review (if you feel it deserves one) would be a most wonderful gift.

The Path to Pivot
If you’re a founder at a crossroads with your startup, keep reading.How many times have you heard that you have to stay the path to get that $1B+ exit? All those stories of grinding it out through the tough years.And yet, some of the most successful companies—Instagram, Notion, Loom, Discord—were the result of giving up on Plan A to go after Plan B (or C or D, etc).Being a founder is full of tough choices. When your startup’s growth hits a wall, you’re faced with two choices: grind it out or start over.So which one is right for you?The Path to Pivot is the practical playbook for founders finding your way to exponential growth. Here’s what you’ll learn:Frameworks to nail the why, when, and how of pivotingDeep dives into the pivots of +10 startups like Actionable tools to rebuild your businessMy StoryI founded my startup in 2011 when I was 24.We got into Y Combinator, raised $1.3M in funding and was profiled in Vanity Fair and TechCrunch…but a year and half into the business, we were floundering. Our growth flatlined and we were forced to pivot. 7 months later we had nothing to show for ourselves and shut down the business.Me with my team, the Dropbox founders, and the YC partnersFailing really sucked. It took me five years to try again.After starting a tech hiring platform in 2017, I again hit a wall. But this time, my cofounder and I executed a successful a pivot into AI tools for gamers, raised new capital and pulled off an exit to FB/Meta in 2020.Today, I run Refactor Labs, where I coach a roster of 10+ founders, senior leaders, and outlier achievers who are reinventing the future.How did this book come to be?In 2022 I started writing about thoughts and experiences with pivots. I started with a series of popular threads on Twitter, later with an unfinished set of essays on Medium.Along the way I started working with the remarkable Rhea Purohit who became my research assistant, editor, and writing collaborator.We realized that there was a lot of good material from my experience, our growing library of pivot case studies, and a lack of credible information about how to think through a pivot.In late 2023, we decided to go all-in on the Path to Pivot, and I’m thrilled to share it with you all today.How this book will help you restart your startup’s growth?If you’re a founder serious about making it big, The Path to Pivot is for you. Just like all great companies, your startup is likely to come up against moments of existential doubt. This book will guide you through the hardest of those trials: the act of pivoting.If you’re thinking about a pivot or in the midst of one, this is your startup’s chance at a stellar second-act.Rebuild with structure and speed. The Path to Pivot lays out immediately actionable tools that help you find your way through the murky, no man’s land of pivoting instead of wasting time flailing on your own. Avoid wild leaps and analysis paralysis; start taking confident, well-informed strides toward success today.Execute proven strategies. I’ve led two startups through pivots: one tanked, one worked. In the book we also breakdown the journey of 12+ startups—from well-known pivots to untold stories you probably haven’t heard before. That means you get to learn from the mistakes and wins of others so that you get it right on your first go.Cut right to the point. There is tons of stuff out there that talks about the problems that startup founders face aka vague business advice you didn’t ask for. I’ve been there. So I wrote The Path to Pivot to be laser focused on the founder or CEO thinking about pivoting or already smack in the middle of one. No one and nothing else.What’s inside The Path to Pivot?Shoot the Zombie: A set of questions to identify if your startup is dying and a guide to transform doubt into courage.Grit, Pivot, or Quit: A 3-part matrix to help you decide whether you should pivot.Pilot Your Pivot: The Align-Explore-Commit framework to test-drive your pivot before going all in.Align Incrementally: A 5-step roadmap to conversations that will align your co-founder, team, and investors on the pivot.Extend Your Runway: A look behind the neat PR announcements from real pivots—learn tactics to reduce your expenses and increase cash flow.Leverage Your Assets: 2 hidden advantages and 6 types of trends you can use to rebuild your business from the ground up.Make The Call: The master blueprint to measure your options before pulling the trigger.Own Your Story: A step-by-step guide to your startup’s brand new story, including the sticky name change questionStay Resilient: 5 tools to better your own health—so that you don’t just survive the pivot, you come out strongerChoose Your VersionNo matter what your budget or stage, there’s a version of this book that’s available for all of you.Friends and Family ($1)—If you’re not sure, you can snag a PDF with the full text of the Introduction and Chapter 1 of Path to Path + 12 one page summaries of all chapters for just one buck + a high resolution PDF of the Path to Pivot framework diagram.Pre-Seed ($15)— PDF, Mobi, ePub and audio version of The Path to Pivot + PDF Seed ($50)—Everything in Basic + Physical copy of The Path to Pivot (200 pages - ships in mid April) + Audiobook version (all chapters complete by mid April) + 12 one page summaries of all chaptersSeries A ($500)—Everything in Pro x 5 (for your cofounders / team to read) AND a private 45 mins Zoom call to discuss your company’s pivot questions / situation.Growth Capital ($5,000)—Everything in Pro x 25 AND 90 mins private workshop for your portfolio companies that are considering a pivot + 90 mins of bookable office hours for 1:1 convos with your founders.No Risk, All RewardI’ve spent years working on the ideas behind “The Path to Pivot” and I’ve talked to so many founders at this point that I’m happy to put my money where my mouth is. If you apply the ideas behind this book and it doesn’t dramatically reset your startup’s trajectory, I’m happy to refund your purchase—365 day money back guarantee.Questions?Contact us at support@pathtopivot.com and we’ll help guide you to your successful pivot.Frequently Asked QuestionsWho is this book for?This book is written for VC-backed founders and CEOs at any stage of a pivot—whether you’re just thinking about it or in the middle of one. It is best suited for the operator of a technology startup, with deep dives into the pivots of companies like Segment, Loom, and Retool. If you’re an indie hacker, non-tech founder, corporate executive, or agency owner, there’s something in here for you as well, but I would recommend you to tweak the advice as needed.What makes this book different from other business books?This book is 70% tactics and 30% theory. It’s a practical playbook for the founder reinventing their business. No vague business advice you didn’t ask for. No fluff. The Path to Pivot is made up of frameworks, tools, and strategies divided into self-contained chapters—so you can dive in and get started right away.Will this book help me decide if I need to pivot?Yes. The first and second chapters of this book are about answering that all-important question. I’ll show you how to use the Grit-Pivot-Quit framework to break down the problem into a series of decisions and guide you through each one.Can this book help me if I’ve already decided to pivot?Absolutely. The Path to Pivot gives you a roadmap to navigate through every single step of your pivot—from strategies for aligning your team to tools to finding your next big idea. It’s divided into self-contained chapters, so it’ll meet you exactly where you are. Dive in and get started right away.Is “The Path to Pivot” relevant for non-tech startups?While the book contains numerous insights from the tech world, the principles and strategies are applicable across various industries. We also include real-world examples from sectors like fashion (GOAT), food (Gobble), and freight (Nuvocargo).How quickly can I expect to see results after reading this book?If you’re dedicated to following this book’s advice, you will be able to:answer the big question—to pivot or not—in 1 weekdevelop conviction around a new direction in 4 to 8 weeksWord of caution: I won’t lie to you—the speed at which you’ll see results depends on the specifics of your situation. In any case, pivoting is not a quick one-and-done fix. If you pivot, you’re signing up for a long road to the big billion dollar exit—this book will guide you through each step. What if I’m not satisfied with the book?I’ve spent years working on the ideas behind “The Path to Pivot” and I’ve talked to so many founders at this point that I’m happy to put my money where my mouth is. If you apply the ideas behind this book and it doesn’t dramatically reset your startup’s trajectory, I’m happy to refund your purchase, no questions asked.

I have pricing tiers starting at $1 all the way to $5,000 so there is surely an option that works for your budget. Pick up a copy for you or perhaps an entrepreneur in your life.

If you want to follow along, I'm halfway through 30 days of posting about pivots (Twitter, LinkedIn)

I'll see you next week.


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How I Can Help You

🧢 Executive Coaching: 1:1 coaching for outlier founders & executives that unlock transformational growth over 4+ month engagements (schedule a call)

📘 The Path to Pivot: A playbook for startup founders who want to reboot their business and get a second chance to swing big (get a copy)

🛠️ Participatory Workshops: Interactive seminars designed to learn and practice crucial skills for navigating complex transitions—storytelling, emotional intelligence, experimentation and more.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

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