Problem Hunting: The Tech Startup Textbook
A practical guide to building a tech startup around a real, measurable customer problem, then lining up marketing, sales, hiring and company values so every part of the business keeps working on it.

Table of Content
1. Introduction
55 sec
Most new founders fall in love with a solution, then spend months searching for someone who wants it. In Problem Hunting, Brian Long, who cofounded the companies TapCommerce and Attentive, argues for the opposite order. Before building anything, ask real buyers about the three biggest challenges in their work, and how they measure them.
That single habit, in Long’s view, is where every healthy startup begins. The problem you uncover becomes the focus of your marketing and the starting point of your sales pitch. Even the company’s values and weekly meetings exist to keep everyone pointed at it.
The book reads as a playbook. It offers an interview script, a document for defining a market problem, a structure for sales calls, a rule for how much of a founder’s time belongs to hiring, and a way to make values appear in daily decisions. Each tool is small enough to try before the month is out.
2. Find a problem buyers will pay to solve
1 min 39 sec
Customers lining up, the industry paying attention, a business model that finally works: every founder wants that moment. Long’s route to it starts somewhere unglamorous, long before anyone writes a line of code.
3. Interview buyers until the problem has numbers
1 min 41 sec
A buyer telling you something is frustrating proves very little. Long’s interview script digs for two things most founders forget to ask about, and they decide whether a problem is worth years of your life.
4. Write marketing busy buyers actually remember
1 min 51 sec
Clever slogans and polished brand names feel like progress, yet buyers walk past them. Long’s approach to marketing sounds almost too plain, and that plainness is exactly what makes distracted people stop and act.
5. Book more sales meetings and close them
1 min 54 sec
Many founders treat selling as something to hire for later. Long sees early sales calls as a source of product insight, and he gives a precise shape for the email, the pitch and the final question.
6. Turn your first fifty customers into advocates
1 min 24 sec
Spending heavily on support for a handful of small accounts looks like poor arithmetic for a cash-strapped company. Long argues those accounts are worth far more than their invoices suggest.
7. Hire builders before bigger companies can
1 min 53 sec
A small startup cannot outbid large firms for talent, yet it still needs exceptional people from day one. Long’s answer involves a demanding rule about the founder’s own calendar and one advantage big companies lack.
8. Make your values show up every week
1 min 44 sec
Most companies write their values once and forget them. Long treats them as working tools, repeated so often that new hires hear them before their first real task, alongside a simple rule for personal focus.
9. Conclusion
1 min 07 sec
Problem Hunting comes back to the number three more than once. Founders ask buyers for the three biggest challenges in their work, and every team member keeps a list of their own top three priorities. Between those two lists sits most of what Long has to teach. A company stays healthy when the problem outside and the priorities inside stay connected, and every message, pitch, hire and meeting is checked against both.
That makes the book a manual of discipline. Long’s tools are modest on purpose: a survey, an interview script, a one-page document, a subject line, a follow-up email.
The first step can happen this week. Talk to a few people who hold a budget in the market you care about. Ask about their top three challenges, the numbers behind them and what they have already tried, and write what you hear into a simple problem document. Then rewrite your next sales email so its subject line names their problem in their own words.
The ideas that become companies are usually the ones someone checked against a real buyer’s problem, early and often.
About this book
What is this book about?
Many startups begin with a product the founder loves and a market that shrugs. Brian Long, cofounder of TapCommerce and Attentive, argues for the reverse order. Before building anything, find out what buyers struggle with at work, how they measure it and what they have already tried. Long turns that idea into a sequence of tools. He shows how to reach consumers with simple surveys and business buyers through the decision-makers who hold budgets, then how to run a structured interview and record the results in a Problem Definition Document. From there he applies the same focus to marketing that names the buyer's pain plainly, sales meetings that open with the problem and end with a clear request, and early customers treated with unusual care. The second half turns inward. Long explains how to hire builders, why founders should give half their time to recruiting, and how to make company values and personal priorities part of every meeting. Readers get a working playbook for the first years of a company, from the first interview to the first fifty customers.
Book Information
Who it's for
Founders unsure of demand
First-time founders with an idea who are unsure whether anyone will pay for it.
Leaders of new startups
Early startup leaders who must hire, sell and set the culture all at once.
Wanting a common playbook
Product, sales and marketing staff at young companies who want a shared, problem-first playbook.
About the Author
Brian Long
Brian Long is a tech entrepreneur who cofounded Attentive and serves as its chairman. The company has grown to more than 1,000 employees. Before that, he cofounded TapCommerce, which Twitter bought for over $100 million. His experience raising capital and leading technology companies gives Problem Hunting its practical, founder-to-founder angle.
Ratings & Reviews
Ratings at a glance
What people think
Listeners consider this title essential reading, offering practical takeaways for those looking to start a business. The flow of the content is well-received, as one listener points out how carefully the chapters have been divided. There is praise for how well it applies to the technology sector, with one listener characterizing the work as a playbook for managing a startup the right way.
Top reviews
This book is essentially a blueprint for anyone trying to navigate the messy early days of a tech startup. Brian Long cuts through the usual fluff found in entrepreneurship guides by focusing on the gritty reality of finding product-market fit. I found the section on hiring 'builders' particularly enlightening, as it shifts the perspective from just filling roles to finding people who actually want to create. While the pacing is fast, some might find the heavy emphasis on sales tools like LinkedIn Sales Navigator a bit too tactical for a general guide. Nevertheless, the actionable lessons regarding the Problem Definition Document (PDD) provide a structured way to validate ideas before wasting capital. It feels like a playbook written by someone who has actually been in the trenches, making it a must-read for first-time founders.
Show moreWow, I wish I had this when I was launching my first venture years ago. The emphasis on achieving product-market fit through rigorous engagement with potential buyers is exactly what most founders overlook. Long explains how to use tools like LinkedIn to find decision-makers and get the feedback necessary to refine a product. The book isn't just about the 'what,' but the 'how,' providing a roadmap for everything from SDR hiring to customer retention. I found the emotional core of the book—the idea that you must be passionate about the problem—to be very resonant. If you are serious about building something that lasts, this book provides the foundational steps to make it happen.
Show moreFinally got around to finishing this, and I’ve got to say, the segmentation of the chapters makes it incredibly digestible. Long divides the journey from ideation to scaling in a way that feels logical and meticulous. The focus on overinvesting in customer support early on is a take you don't hear often enough in the 'move fast and break things' culture. However, some sections on aggressive case study funding felt a bit repetitive towards the end of the book. It’s a solid resource for tech-heavy founders who might be great at building but struggle with the marketing and sales side of the house. Truth is, the advice on creating urgency in your messaging is probably the most valuable takeaway here.
Show moreBrian Long doesn't pull any punches here, offering a high-octane guide to the startup lifecycle. The way he breaks down the transition from finding a problem to building a team of 'builders' is genuinely impressive. I particularly enjoyed the section on the Problem Definition Document; it’s a tool I’ve already started implementing with my own team to ensure we aren’t just chasing ghosts. Frankly, the pacing is so fast that you might need to read it twice to catch all the nuances of his recruitment strategy. While some might find the focus on aggressive sales a bit overwhelming, it’s a necessary reality check for founders who think a good product sells itself. This is a practical, no-nonsense roadmap.
Show moreAfter hearing about Brian's success with Attentive, I had high hopes for this book, and it mostly delivered. It reads like a playbook for running a startup correctly, with a heavy emphasis on data-driven decision-making. I loved the focus on 'builders' and the rejection of the 'perks-as-culture' myth that has plagued Silicon Valley for too long. My only real complaint is that the marketing section feels a bit repetitive with its heavy reliance on case study funding. Still, the core message about aligning your product development with validated customer needs is timeless. It’s an essential addition to any founder’s library, providing a clear path through the noise of the tech world.
Show moreAs someone who has worked in tech for a decade, I found the core concepts here to be a mixed bag. The title 'Problem Hunting' suggests a deep dive into discovery calls and ideation, yet a massive chunk of the text is devoted to sales and scaling. Truthfully, if you are looking for a guide on how to interview users, you might find this a bit lacking compared to other specialized texts. That said, the discussion on building a company culture through values rather than perks is spot on. Long argues that culture is about decision-making, not ping-pong tables, which is a refreshing perspective. It’s a decent read for the recruitment advice alone, especially the part about the first ten employees.
Show moreEver wonder why most startups fail within two years? This book suggests it’s because they solve problems that don't actually exist or lack the right team to execute the solution. I appreciated the specific tools mentioned, like using LinkedIn Sales Navigator and Google Forms to gather real-world data early. The writing style is direct and leans heavily into the 'playbook' feel, which keeps you engaged without getting lost in theory. One minor gripe is that the tone can be a bit prescriptive at times, almost as if there is only one way to scale. If you're building an enterprise SaaS company, this is gold, but consumer-facing founders might need to adapt these specific strategies.
Show moreThe chapter on the Problem Definition Document was worth the price alone, but the rest of the book felt a little uneven. It starts strong with ideation and validation, but then it spends a disproportionate amount of time on sales tactics and CRM tools. In my experience, the hardest part of a startup is the very beginning, and I wish there was more depth there. The advice on hiring is solid, though—specifically the idea that your first ten hires define your trajectory for years to come. It’s a good book for a weekend read, but don’t expect a deep philosophical inquiry into entrepreneurship. It’s more of a tactical manual for growth than a book on ideation.
Show moreTo be fair, the advice is solid but feels very specific to the enterprise SaaS world where Brian Long has made his mark. If you’re building a niche consumer app, the heavy focus on SDRs and LinkedIn Sales Navigator might not apply to your daily grind. I did appreciate the meticulous segmentation of the chapters, which makes it easy to jump around to the sections most relevant to your current stage. The section on one-on-one meetings and team alignment was surprisingly insightful for a book that spends so much time on sales. It’s a middle-of-the-road read for me because of the narrow focus, but for the right audience, it’s easily a powerful manual.
Show moreNot what I expected based on the title, to be fair. I was hoping for a masterclass in the 'hunting' phase—the messy, early-stage discovery of a pain point. Instead, the book pivots very quickly into sales development representatives (SDRs) and aggressive marketing tactics. Look, the advice is functional, but it feels like it belongs in a book called 'Sales Scaling' rather than one about finding a problem. There is a lot of talk about investing heavily in personnel and sales, which feels like a strategy reserved for those with deep VC pockets. If you aren't already funded, some of these 'essential' steps will feel completely out of reach. It’s okay, but it lacks the nuance of lean startup methodologies.
Show moreQuestions about this book
What is the main idea of Problem Hunting by Brian Long?
Long argues that a tech startup should begin with a real, measurable customer problem, found by interviewing buyers about their top three work challenges, the metrics behind them and what they have tried. That problem then guides everything else: marketing that names the pain plainly, sales pitches that open with it, hiring of builders who want to solve it, and values and priorities that keep the team focused on it.
What is a Problem Definition Document?
It is a written record of what you learn from buyer interviews. Long’s version lists the industry, the market size, the buyer roles, the specific problems, the metrics that show them and the solutions people have already tried. His example is an online retailer whose email marketing is declining, measured through open rates and click-through rates. The document helps prove a problem matters and points toward possible solutions.
How does Brian Long recommend running a sales meeting?
Start with discovery questions about the buyer’s needs. Then give a short pitch that covers the problem, your solution and why it matters to them, always putting the problem first. End with clear next steps and ask for the sale before the meeting closes, for example by asking whether anything would stop them trying the product. Afterward, book a follow-up and send a summary email.
How much time should founders spend on hiring, according to Problem Hunting?
Long says at least half of a founder’s time should go to building a pipeline of candidates through networking, meetups, target lists and personal messages, with persistent follow-up. He sets the highest bar for the first ten employees, since they shape culture and recruit others, and he urges speed, calling it a startup’s greatest hiring advantage over larger companies.
Who should read Problem Hunting?
It suits first-time tech founders, early employees and anyone building a young company who wants concrete steps instead of theory. The book covers finding product-market fit, writing clear marketing, booking and closing sales meetings, caring for the first fifty customers, hiring builders and turning company values into daily habits, so it works as a single reference for the early years.
Readers also enjoyed
Alibaba: The House That Jack Ma Built
Duncan Clark
7 Powers: The Foundations of Business Strategy
Hamilton Helmer
Bad Blood: Secrets and Lies in a Silicon Valley Startup
John Carreyrou
AUDIO SUMMARY AVAILABLE
Listen to Problem Hunting in 15 minutes
Get the key ideas from Problem Hunting by Brian Long, plus 5,000+ more nonfiction titles.
- 5,000+ titles
- Listen as much as you want
- 7-day free trial
- Cancel anytime



















