From operational excellence to recruiting, Attentive co-founder (and current Executive Chairman), Brian Long, shares advice for any leader who’s launching something new. 

Brian Long co-founded Attentive in 2016, and served as the company’s CEO until 2023, when he transitioned to being Executive Chairman of the board. Early on, he saw the opportunity to transform how brands engage with consumers. He is currently working on something new. We had a chance to talk with him about his recently-released book, Problem Hunting, a step-by-step guide to building and running a tech company. Take a listen to the interview or check out the recap below. 

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You grew Attentive from your living room into a global business. And before that, you sold your startup, TapCommerce, to Twitter. How did these experiences shape your approach to leadership?

To me, the CEO and founder's job ultimately boils down to three things: 

1. Setting an overall vision for the business. That includes identifying the problem you're solving and building the solution to do that.
2. Finding great people to work with you on that problem.
3. Securing the financing to pay for your employees, along with the research and development to build your products. 

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What inspired you to write your new book and what do you hope readers will take away from it?

I’ve been getting introduced to a lot of entrepreneurs—people at earlier stages in their careers looking for advice. I was doing a couple of meetings a week, and they often ran over. People always had follow-up questions and wanted to go into more detail, and I felt like I was answering the same questions over and over again. So I figured, why don't I just make a Google Doc to share my standard answers? 

Around the same time, a book publisher reached out to me to see if I'd be interested in writing a book. I said, "Actually, I've got this Google doc that could be a book…" They were totally on board. 

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That’s awesome. What was the writing process like for you? Did you work with anybody or was it all something that you did yourself?

I had considered working with a co-writer or a ghost writer. But when I spoke to other business writers that had hired a writer, they found the end result really wasn't written in their voice. It felt watered down—like it wasn’t their book anymore.

So, I decided to write it all myself. When it came time to edit it, I had a publisher who helped me focus on certain sections, and a copy editor who handled all the grammatical work. 

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Was there a book that you found really helpful when you were starting out as a founder?

I really liked the book "How to Win Friends and Influence People" by Dale Carnegie. The title is a little cynical, but the content is fantastic. It breaks down very practical advice. And even though it was written in the 1930s, the advice Carnegie shares is timeless and applicable today.

When I was writing my book, I wanted to make something very practical, too—almost like a textbook to help anyone start a tech company. 

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How did your experience leading Attentive through different stages of growth (and macro industry changes) prepare you for writing this book?

This book is very focused on the early stages of building a company: The core steps to finding a problem you want to solve, and then working on the solutions to solve that problem. I think the steps I share in the book can be applied to any macro environment. 

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Your book offers a tactical playbook for tech founders. What lessons can retail and e-commerce marketing leaders learn from your book?​​

Every company is a tech company at its core. I wrote the book for anyone who wants to start a business—whether it’s your ‌first time, or you're a seasoned veteran, hopefully you’ll find some tips and lessons to take away. You’ll find chapters on identifying the initial problem in the market and how to approach solving that problem. That’s definitely something retail and e-commerce leaders are thinking about—how to solve consumers’ problems. 

And there are chapters on things every company needs to do well: Recruiting and building a great team, managing the culture of a company, and the operational side of things, including strategies for running exec, 1:1, and board meetings. All of these things are fundamental to running any great business.

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Can you tell us about a particular challenge or learning experience during your time as CEO of Attentive that was particularly impactful?

Something not everyone might know is that we pivoted Attentive’s business early on. One enduring lesson I learned from that process is that people tend to be very polite, and as a result, it's very hard to get critical feedback. 

We had an initial product we thought people wanted and liked, but then when we built it and went out to sell it, it turned out no one really wanted to buy it. Everyone was just being polite and telling us it sounded great.

I've found that a really useful mechanism to solve for this problem is when you want to get someone's feedback on something, you can say, “What do you think about this?” Most people will say, “It’s good.” Follow up and ask them, “On a scale from one to 10, how would you rate how you feel about this?” If they give you any score under an eight, that's negative to neutral. I'm amazed how many times I've done this and thought that a person really loved what I was showing them… until I would ask them for a rating. 

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Knowing what you know now, what would you have done differently? 

That’s a hard question! But here’s one. When we were a smaller company, we had eight company values. And in the transition to becoming a larger company, we decided to revisit and narrow our values down to four. But there’s one value that got cut that I would have kept— “lots of laughs.” Life is short and you gotta have fun doing what you’re doing. Having a generally positive outlook and creating a fun environment just makes life better for everyone. And that's what lots of laughs entails for me. 

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There’s been a lot of talk about this being the single greatest moment of innovation of our time. What advice would you give to founders (or marketing leaders) who are in the thick of either starting something new or trying to reinvent their business?

I'd challenge them to ask themselves this question every week: What is the boldest thing I could do in my business? And if by the third or fourth week you still aren't doing it, ask yourself, what's holding me back?

Most people (and companies) get into a certain cadence of continuing to do the same things over and over again. Every day, they’re deciding to keep doing the same thing—they just don't see it that way.

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What do you see as the biggest challenges facing retail and e-commerce marketers today? If there’s one piece of advice you could give them, what would it be?

I think the biggest problem that marketers are faced with today is probably macro. A lot of demand and activity got pulled forward by the pandemic, and now it's getting pulled back. If I was a retail or e-commerce marketer, I'd use this time to re-evaluate my priorities. 

When you're in wild boom times, you tend to overlook a lot of gaps in your business and as a result, a lot of stuff can get messy. Maybe that’s reflected in an unclear product road map, unnecessary product operations, or a dip in product quality. In less crazy times, you can really tighten up your operations and ask yourself why you're doing the things you're doing. 

Thanks for taking the time to chat with us, Brian. You can find his book on Amazon, Barnes & Noble, and Bookshop. 

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