Brian LongProblem Hunting: The Tech Startup Textbook

“As the saying goes, trust and reputation are built over a lifetime and can be ruined in minutes.”I’ve been fortunate to have been on many different types of teams throughout my life from youth soccer to high school mock congress to division 1-aa football (important to note that ‘on the team’ for one season does not imply ‘contribute’ to in-game success), corporate audit, international dry-bulk export handling, etc..The one constant of a successful team is a leader or leaders who are able to make their players/teammates feel better about themselves. I remember my first tee-ball coach. That ability came so naturally to him, that going forward, it made it harder for me to participate on teams whose leaders did not share that similar trait (Don Berger via Chris Berger: thank you).If you’ve made it this far, chances are, you enjoy reading, too. If you’re like me, maybe you agree that one of the greatest joys of loving a book is connecting with that feeling that when you’re about to finish it, you just don’t want it to end. After FINALLY starting The Boys in the Boat in 2024 and finishing it in 2025, I began 2025 with a commitment to start and finish twelve new books for the twelve-month calendar year.The sub commitment was that my first start to finish read would be: Problem Hunting: The Tech Startup Textbook by Brian Long (note: no different from having ZERO in-game college football varsity playing experience, I also have ZERO tech experience).I’ve known Brian for over 22 years and for the past 15+ (years), he has been building, growing, and leading teams: motivating brilliant, ambitious doers to communicate better, trust one another, to achieve shared visions and meet common goals. Over the course of the 260 page Problem Hunting journey, common themes continued to be built upon, the content kept getting better, the stories more relevant than the ones prior, and I just didn’t want it to end. But it did.I can’t thank Brian enough for putting his heart and soul into writing this book, citing all the other motivators and teammates who have made his incredible journey possible. His courage is commendable, but what will always be more exciting for me is his willingness to continue to put others first, getting all of us to believe in ourselves and our potential together.

As an aspiring entrepreneur, the handful of similar booksI’ve read have always been much more theoretical/top down and I personally find less helpful. I particularly love how this book is written pretty much solely with concrete examples. For example, Brian puts the high performing outbound email the Attentive team used to get their meetings, the cold email he uses to get his early funding (and spoiler it’s not to spend all your energy solely msging the VC but actually to the founders of the companies the VC has invested in to get an intro booooom haha). I mean just using solely this fundraising idea to be more successful fundraising pays for the book infinitely over.One of my other favorite parts is when Brian shares the interview questions his team would ask, such as “how would you rather your performance on a scale of 1-10” and anything less than 8 counterintuitively actually being the “correct” answer over a 9 or 10 because it shows the individual is more receptive to feedback and ways to improve. And then Brian will provide his follow up question and then a SECOND follow up question of what would you change next time” which really gives more context to how the candidate thinks. This is an example of what I mean by this book is written as granularly possible and thus, personally what I find most helpful.Books are such a beautiful thing, how wonderful it is to get all this value condensed in such an easy to read book. What a treat, thank you Brian Long!

Working at Attentive Mobile pre-Series A was nothing short of the most exhilarating roller coaster adventure of my life. I had the privilege of experiencing Brian Long’s relentless pursuit of greatness and his calculated approach to problem-solving firsthand. At first, I’ll admit, it took me a while to fully grasp his unique approach. But what stood out was his uncanny ability to consume data points from every division of the company and articulate them in real-time, whether in internal meetings or client conversations.Reading “Problem-Solving” was like reliving that incredible journey, but with a newfound depth of understanding and appreciation. One of the most impactful takeaways for me was realizing how Brian’s holistic understanding of the company’s operations empowered him to have meaningful conversations with clients and prospects. This wasn’t just about solving problems; it was about understanding needs at a granular level, which in turn allowed us to build meaningful products and carve out a new category in the industry.This book is more than just a read; it’s a blueprint and a methodology that has the power to change the trajectory of future entrepreneurs who embrace it. It’s a treasure trove of insights that Brian has generously shared, and I’m beyond grateful for the opportunity to have worked alongside him. As I venture into my next chapter, I’m confident that the wisdom packed into these pages will continue to provide immense value.If you’re an aspiring entrepreneur or someone keen on understanding the mechanics of problem-solving in a fast-scaling company, this book is your golden ticket.