Guest: Brian Long, former CEO of Attentive and author of Problem Hunting: The Tech Startup Textbook

Brian Long’s most recent company, Attentive, was originally designed to help clients communicate with their distributed workforce — but about six months in, he and his co-founder realized that that business would not grow as quickly as they had hoped. So, they decided to pivot to SMS marketing, at the cost of a few dubious employees and a well-known Fortune 500 client. The successful pivot confirmed Brian’s belief that it’s possible to over-commit to one solution, when in fact there may be bigger and better problems to solve. “I’ve just seen so many entrepreneurs spend years of their life building something being stuck with it,” he says, “and then trying to figure out how to fit it into something that doesn’t work.”

In this episode, Brian and Joubin discuss zero to one building, the problem with how entrepreneurs solve problems, How to Win Friends and Influence People, Matt Mochary, Tom Mendoza, transactional relationships, the dangers of ego, optimists and realists, best man speeches, defining a unique culture, reverse selling, Lunar Holdings, Peter Reinhardt, marketing conservatively, and business book sales.

In this episode, we cover:

New York vs LA (00:54)
How Brian feels, six months after stepping away from the CEO role (02:37)
Product-market fit and TAM modeling (06:07)
Build last (09:05)
The qualities of great entrepreneurs (13:24)
Tap Commerce and starting in sales (15:49)
Listening and remembering names (20:40)
The day after selling Tap Commerce (23:32)
Starting another company, Attentive (25:07)
Resilience and optimism (29:21)
Fear, doubt, and the worst-case outcome (32:50)
What Brian would tell his 29 year old self (37:13)
Hiring and pivoting at Attentive (41:17)
Text message marketing (45:49)
How Brian interviews people (50:12)
His new holding company, Lunar and its first startup (51:52)
Don’t go social (55:21)
What Brian is personally excited about and what “grit” means to him (01:01:57)

Links:

Connect with Brian
- LinkedIn
- Buy Brian’s book, Problem Hunting: The Tech Startup Textbook
Connect with Joubin
Learn more about Kleiner Perkins
This episode was edited by Eric Johnson from LightningPod.fm

#166 Executive Chairman and Former CEO Attentive, Brian Long: Problem Hunting

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