Problem Hunting

Problem Hunting Plot Summary

Introduction

Starting a business is often portrayed as a glamorous adventure, but the reality is that entrepreneurship is about solving genuine problems. Every successful venture begins with recognizing an unfilled need or addressing a burning pain point in the marketplace. What separates thriving entrepreneurs from those who struggle isn't just passion or funding—it's their ability to identify problems worth solving and create solutions people actually want. The path to building a profitable business requires more than just good ideas. It demands a systematic approach to finding problems, validating solutions, assembling the right team, and communicating your value to customers. Throughout this exploration, we'll examine practical frameworks for transforming market gaps into business opportunities and learn how successful founders navigate the complex journey from initial concept to sustainable venture. This entrepreneurial mindset—seeing obstacles as opportunities and turning problems into profit—is what ultimately creates businesses that not only survive but thrive.

Chapter 1: Find Your Burning Problem

The foundation of any successful business isn't a brilliant idea—it's finding a genuine, pressing customer problem. Brian Long, who built and sold TapCommerce to Twitter for approximately $100 million, emphasizes that problem hunting is serious work that requires deep listening and trust-building with potential customers. When Long started Attentive, a text message marketing platform, he didn't begin by building technology. Instead, he methodically analyzed different market categories, looking for industries with significant revenue and growth potential. He discovered that while eCommerce was booming, companies were struggling with a critical problem: their ability to reach customers through traditional channels like email was declining dramatically. Email open rates and click-through rates were plummeting, directly impacting revenue. This represented a burning problem—one that businesses would pay to solve. Long's approach involved creating a structured problem definition document (PDD) that clearly articulated the issue. For Attentive, the PDD highlighted that eCommerce companies were seeing email marketing performance decline by 75% over eight years, with metrics showing lower open rates and engagement. The document outlined not just the problem but quantified it with specific metrics that showcased its severity. To validate problems effectively, Long recommends developing a systematic interview process. First, confirm basics about what the person does to understand their role. Then ask directly: "What are the top three problems in your job today?" For each problem mentioned, dig deeper with follow-up questions: Why is it a problem? What metrics track this issue? What have they tried that hasn't worked? Most importantly, have them rate each problem on a scale from 1 to 10, with anything below 8 suggesting it's not truly urgent. When evaluating potential problems, remember that markets change constantly. Some problems are temporary and will disappear, while others represent fundamental shifts that create long-term opportunities. The best problems to tackle are those rated 9-10 by multiple potential customers, indicating they're truly "burning issues" worth solving. Make sure you genuinely like the problem area you're exploring. As Long discovered when briefly working on a used clothing marketplace, if you don't find the industry interesting, you'll struggle to maintain the motivation needed for the entrepreneurial journey. By spending time talking to people in your target industry before fully committing, you can save yourself years of working on problems you don't truly care about.

Chapter 2: Build Solutions That Actually Work

After identifying a genuine customer problem, resist the immediate urge to build a product. This is where many entrepreneurs fail—they create solutions without validating whether customers actually want them. Brian Long learned this lesson personally when developing a website called Hungry4 that allowed users to search restaurant menus, only to discover that consumers wanted something entirely different. At Attentive, Long took a more methodical approach. He created a Solution Specification Document (SSD) that built upon his Problem Definition Document. The SSD defined specific metrics of success: sign-up rate for text messages, open rate, click-through rate, and revenue generated. Then he outlined minimum product requirements to test these metrics. This framework forced clarity about what would constitute a successful solution before writing a single line of code. The next step was turning this document into a pitch for potential customers. Long created a simple deck that followed a clear structure: overview of the problem (declining email performance), solution (text message marketing), and getting started. The deck used data visualizations showing email marketing click-through rates dropping by almost half over six years, creating urgency around the problem. Then it introduced SMS as a solution with 10X higher engagement rates. Long discovered that getting honest feedback requires special tactics. People naturally avoid giving negative feedback, so he implemented a structured post-pitch verbal survey asking specific questions: How much is this problem an issue (1-10)? How interested are you in this solution (1-10)? What do you like most? What do you wish was different? By analyzing patterns in these responses, Long could determine if his solution truly resonated. Before building anything, Long made potential customers commit. At Attentive, they required verbal commitments from multiple businesses willing to try the product. Only after securing these commitments did they build their minimum viable product—and even then, they cut the planned features by 50% to get to market faster. They eliminated a web application for viewing message performance and analytics dashboards, replacing them with simple Excel sheets emailed to customers. This approach allowed Attentive to launch quickly, gather real customer feedback, and iterate based on actual usage rather than assumptions. By testing solutions thoroughly before building, they avoided wasting resources on features customers didn't want and focused exclusively on solving the core problem: helping businesses reach customers more effectively than email.

Chapter 3: Cultivate a Team of Passionate Builders

Finding the right people for your startup is arguably more important than your initial product or business model. Brian Long discovered this truth across multiple ventures, learning that the first ten employees have an exponential impact on a company's trajectory—they recruit the next forty, set cultural norms, and make pivotal decisions that shape the business. When starting TapCommerce, Long struggled to build a strong initial team. As an unproven entrepreneur, he couldn't attract top talent, resulting in a relatively inexperienced group. For Attentive, he took a completely different approach, focusing intensely on hiring what he calls "builders"—people who love to make things, work hard, and take ownership without needing extensive direction. These individuals often have ambitious goals, demonstrate pride in prior accomplishments, and genuinely enjoy the process of creation. To identify builders during interviews, Long developed specific questions: "What is your dream job and why?" (looking for ambitious goals), "What is your greatest accomplishment?" (assessing pride in their work), and "Can you think of something you built that you're proud of?" (evaluating their building mindset). He also probed for coachability by asking candidates to rate their interview performance and suggest improvements, demonstrating their ability to receive feedback. For Attentive's sales development roles, Long's team used a creative interview technique where candidates were asked to pitch their favorite book. The best candidates would first ask questions to understand the interviewer's interests before crafting their pitch—showing natural sales instincts. When asked to rate their pitch performance, those who gave themselves modest scores and identified specific improvements demonstrated the coachability essential for growth. Long recommends spending 50% of your time on recruiting during the early stages of company building. For Attentive, fourteen of the first twenty hires came through completely cold outreach. This required creating detailed lists of target companies and roles, then using LinkedIn and other platforms to send personalized messages. Persistence proved crucial—most candidates didn't respond to initial outreach, but Long's team continued following up, sometimes requiring ten touchpoints before securing a meeting. For interviewing, Long advocates creating detailed question templates tailored to each role, with questions directly mapping to required skills. Each interviewer records candidates' responses and assigns 1-10 scores, creating objective data for comparison. A "hiring committee" reviews results and requires at least one person to "champion" each hire, taking personal responsibility for the candidate's success—a system that ensures alignment and accountability. The ultimate advantage startups have in recruiting is speed. While larger companies offer bigger brands and higher salaries, they move slowly. By compressing the entire hiring process into 2-3 days and making generous first offers, Long's startups consistently won talent that larger companies coveted.

Chapter 4: Create Marketing That Speaks to Customer Pain

The most common marketing mistake entrepreneurs make is focusing on their solution instead of the customer's problem. Nobody cares about your product—they care about their problems and what you're doing to solve them. Brian Long learned this lesson firsthand when launching Attentive's marketing efforts. Initially, Attentive sent emails with subject lines like "Interested in SMS Marketing for YourBrand" and "SMS marketing reaches 90%+ open rates." These solution-focused messages generated little interest. When they shifted to problem-focused messaging like "20% more revenue, free trial" and "Make [custom estimate] for [brand name]," response rates skyrocketed. The difference wasn't the product—it was speaking directly to the customer's burning need for revenue growth. Long emphasizes that naming your company and product deserves far less attention than most founders give it. For Attentive, they operated with AttentiveMobile.com for six years before acquiring Attentive.com. The company name matters far less than clear messaging about the problem you solve. Every successful tech company has changed names at least once—Google began as "BackRub," and Facebook was initially "TheFacebook." Your name will likely evolve as your business does. For effective marketing, Long recommends creating messaging that states what your company does in clear, jargon-free language. Attentive's early website headline read: "Discover a way to drive 20% more revenue... using Text Message Marketing." As text messaging became more recognized, they simplified to: "Attentive: The most comprehensive text message marketing solution. Attentive will make SMS your next top 3 revenue channel." Clarity always trumps creativity. Repetition is another crucial marketing principle. When Long pitched a product called "CommentSurf" to a potential customer, after fifteen minutes the buyer asked, "Why would I want you to write articles for my website?"—completely misunderstanding the product. Entrepreneurs live and breathe their solutions daily, but buyers may only have brief exposure. Long recommends saying important points at least three times throughout your marketing materials. To build credibility rapidly, Long created a customer conference for Attentive just three months after launching, when they had only a handful of customers. They invited everyone they knew from reputable companies to assemble an impressive logo list, hired videographers to capture testimonials, and generated content that made the company appear more established than it was. Before the event, Attentive was signing two to three customers monthly; after leveraging this content across their marketing channels, they consistently signed over ten customers per month. The ultimate goal of marketing should be category leadership. Look at the most valued companies globally—Apple, Microsoft, Google, Amazon—nearly all are category leaders. By positioning Attentive as the definitive text message marketing solution rather than diversifying into related areas, they created a clear identity that customers and investors could easily understand and remember.

Chapter 5: Master the Art of Sales Conversations

Sales is often viewed as a necessary evil by technical founders, yet Brian Long credits his sales experience as the biggest reason for his entrepreneurial success. At Attentive, he discovered that buyers don't remember presentations—they remember people. In one revealing instance, a customer accidentally left their video call running after an Attentive sales presentation and discussed it with colleagues: "That guy who looked tired with the gray hair was the CEO. They were really paying attention and listening to us. They seem to really care. We should go with them." Nothing was mentioned about the product features or statistics. Long emphasizes several tactical elements that dramatically improve sales meetings. First, always turn on your video. According to a Zoom survey, 67% of professionals say video increases engagement, and 70% report greater trust between them and potential clients when video is active. Second, have a second person on every call—a silent, no-video participant who takes detailed notes, allowing the primary presenter to focus entirely on the conversation. One of Long's most powerful techniques is what he calls "the golden silence." After a potential customer finishes speaking, most salespeople immediately jump in with a response. Instead, Long recommends waiting and continuing to take notes. This accomplishes two things: it shows you're truly listening, and it creates space for the customer to continue talking. In one meeting with a chief marketing officer in Texas, this technique led the executive to share frustrations with their current vendor and specific requirements for a new solution—crucial information that might never have surfaced without patient silence. The structure of a sales call is equally important. Long begins with discovery questions to understand the customer's situation, followed by a concise "elevator pitch" that explains the problem, solution, and why the buyer should care. For Attentive, they included a "sit-up slide" that made a bold claim about revenue potential, designed to grab attention and spark engagement. The remainder of the presentation focuses on the customer's problem, Attentive's solution, and clear next steps to implementation. When closing sales, Long targets the three main sources of friction: risk, time, and money. For Attentive, they discovered that enterprise buyers worried about lost email revenue, legal regulatory concerns, and consumer annoyance. They built specific product features to address each concern. To reduce the time barrier, they created a completely free trial with minimal integration requirements. For cost objections, they eliminated upfront fees entirely. Long's most important closing advice is simple: ask for the sale. At the end of every meeting, he directly asks, "Are there any reasons you wouldn't try this out?" If customers can't commit immediately, he schedules the next meeting before ending the call—if they won't schedule a follow-up, it signals they're not truly interested. Finally, he emphasizes that "whoever wants it the most will win." The company willing to put in extra effort—flying to meet a client on short notice, staying up all night to complete a proposal, or finding creative ways to demonstrate commitment—usually gets the deal.

Chapter 6: Secure Funding That Fuels Growth

Raising capital is often portrayed as a mysterious art, but Brian Long approaches it like any other sales process: understanding your buyer, building relationships, and removing friction at every step. Over his career, Long has raised approximately $850 million for his ventures, providing valuable insights into how the venture capital ecosystem works. For TapCommerce, Long completed fifty-two investor meetings to find the few who said yes. The process took about four months with numerous false starts. During one fundraising round, Long had nearly accepted a term sheet when he received a last-minute offer to visit an investor in Boston. Despite having another offer in hand, he made the trip—and received a term sheet at twice the valuation of his existing offer. This experience taught him to "take the extra meeting" and never stop the fundraising process until money is in the bank. Long recommends treating your pitch deck like a sales presentation, with sections covering: the problem (declining email performance), your solution (text messaging platform), traction (customer growth and retention), and a big vision for the future. The most effective pitches tell a story investors can easily retell to their partners. For Attentive, the narrative was simple: "Companies are struggling to communicate with customers. Email marketing click-through rates have decreased by 75% over eight years. Attentive is personalized text message marketing that drives 10X higher revenue per message than email." To get meetings with investors, Long creates spreadsheets of funds that have invested in similar companies, then asks fellow entrepreneurs for introductions. Warm introductions work significantly better than cold outreach, as early-stage investing is built on trust. When approaching entrepreneurs for introductions, Long sends a simple note: "I noticed [Investor Name] invested in you. Have you had a good experience? Would you mind forwarding this note to see if they would be interested in my company?" During fundraising, Long emphasizes complete honesty. Many entrepreneurs falsely claim they have term sheets to create urgency, but investors quickly discover these lies, destroying trust. Instead, Long recommends transparency about where you are in the process. After pitches, he directly asks investors to rate their interest on a 1-10 scale, then follows up with "Why do you feel that way?" This provides actionable feedback while clarifying their true interest level. For early-stage companies, Long recommends using convertible notes or SAFEs rather than complex stock purchase agreements. These simpler instruments allow faster closing and avoid complicated valuation discussions. For Series A and beyond, term sheets require careful negotiation of key elements: valuation, board composition, liquidation preferences, and voting rights. Perhaps most importantly, Long emphasizes preparation. Before starting fundraising, he assembles comprehensive diligence materials including the fundraising deck, cap table, financial forecast, and sales materials. This professional approach signals to investors that the company is well-managed and ready for capital. After receiving a term sheet, companies should move quickly to close—typically within 2-4 weeks—to minimize market risks and ensure the funding actually arrives. The ultimate lesson from Long's fundraising experience is persistence. Behind most "overnight success" fundraising stories is a tremendous amount of work, preparation, and resilience in the face of rejection.

Summary

The entrepreneurial journey begins and ends with solving meaningful problems. Throughout this exploration of Brian Long's experiences building multi-million dollar companies, one principle remains constant: successful businesses aren't built on clever ideas but on addressing genuine customer pain points with elegant solutions. From identifying burning problems and validating solutions to assembling passionate teams and securing funding, every step requires systematic thinking and relentless execution. As Long powerfully states in his closing remarks, "Life is short. Time goes very fast. No one else is really going to care what you do unless you solve a big problem for them." This truth liberates entrepreneurs from worrying about others' opinions and focuses them on what matters—building solutions that create value. Your entrepreneurial journey starts today by identifying a problem you genuinely care about solving, then systematically applying these principles to transform that problem into a profitable, purpose-driven venture. The greatest opportunity lies not in following others' paths but in addressing problems you're uniquely passionate about solving.

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Brian Long

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