An Early-Stage Founder Belongs In the Trenches (Lesson #8 of 8 Lessons Growing 8 Companies)

An Early-Stage Founder Belongs In the Trenches (Lesson #8 of 8 Lessons Growing 8 Companies)

All those important lessons you learn over the course of a career can actually hurt you if you don’t know when to set them aside. You have to see when it’s not a time to be the seasoned CEO and instead lean into your role as the scrappy founder — even if this isn’t your first (or your seventh) rodeo.

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Tech Entrepreneurs Can't Do Everything (Lesson #7 of 8 Lessons Growing 8 Companies)

Tech Entrepreneurs Can't Do Everything (Lesson #7 of 8 Lessons Growing 8 Companies)

Being part of building a seventh company taught me many things. It taught me that tech entrepreneurs can’t do everything — more than that, I learned that honesty about how your skills and expertise line up with what you’re trying to build is much more important than a passion for what you’re selling.

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Results Aren’t Achieved When Values Don’t Align (Lesson #6 of 8 Lessons Growing 8 Companies)

Results Aren’t Achieved When Values Don’t Align (Lesson #6 of 8 Lessons Growing 8 Companies)

In 2005, I was working as a consultant, doing some due diligence on software for a startup. The company, founded by two patent attorneys, was attempting to create an online marketplace for swapping books, music, movies, and video games—back when those were all physical objects that needed to be physically traded. The founders had patented their ideas and written hundreds of pages of specs. They’d already hired, fired, and had sued one software development firm. When the second firm they’d hired went past budget on a fixed price contract before completing the software, the founders reached out to me.

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Two Wrong Leaders Don’t Make a Right One (Lesson #5 of 8 Lessons Growing 8 Companies)

Two Wrong Leaders Don’t Make a Right One (Lesson #5 of 8 Lessons Growing 8 Companies)

The experience left a big impression on me. Leadership isn’t theoretical. There are real, perhaps even dire, consequences to poor leadership. Fudging it doesn’t work, and pretending that two wrongs add up to a right could end with you thanking your lucky stars that you don’t have to explain to your board how you blew up a BMW test engine.

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The Best Growth Strategy is to Make Yourself Dispensable (Lesson #4 of 8 Lessons Growing 8 Companies)

The Best Growth Strategy is to Make Yourself Dispensable (Lesson #4 of 8 Lessons Growing 8 Companies)

It took me three years to go from VP Engineering to CTO to COO to CEO. How does someone grow that quickly? Yes, I worked hard and focused on results. Yes, I was afforded an opportunity being at a good place at a good time. Still, no amount of hustle, talent or luck could have made such a rapid transition successful. What made it possible?

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It’s All About the People, the Team, and its Values (#3 of 8 Lessons Growing 8 Companies)

It’s All About the People, the Team, and its Values (#3 of 8 Lessons Growing 8 Companies)

As a leader or entrepreneur, you get to create vision, set goals, and define success. As a business coach, I’d be negligent if I didn’t say that money (revenues & profits) is important. A business needs to be able to sustain itself (and its principals, team, investors, etc.). To make money, we need people. To attract and keep people, we need team and well-defined values. There is a direct relationship between money, people, values, culture, and organization. Who you hire and how you lead and build team is critical to the long term success of anything you may undertake where organization is necessary.

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Why You Need Access to Inspiration and Experience (#2 of 8 Lessons Growing 8 Companies)

Why You Need Access to Inspiration and Experience (#2 of 8 Lessons Growing 8 Companies)

Amidst the tension, I was making every rookie management mistake in the book. Except I didn’t even have a book. I had no management experience and no training, nor did anyone around me. I made hiring mistakes. We were offered a course on Behavioral Interviewing, (which was the best thing I learned and saved my book, 20+ years later, pictured here), but even with the training, I put the wrong people in the wrong jobs. I recall my QA Manager being a disaster. There were other performance issues on my team. Wondering what to do when I found an employee sleeping under his desk. I didn’t know how to handle any of them. I tried to use my engineering skills to fix the problems, but you can imagine how that turned out.

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Good Leadership is a Prerequisite for Good Business (#1 of 8 Lessons Growing 8 Companies)

Good Leadership is a Prerequisite for Good Business (#1 of 8 Lessons Growing 8 Companies)

The first lesson came from my time at KnowledgeSet Corp in the late 1980’s. KnowledgeSet (KSC) was a pioneer in the early PC days, one of the first to put data on a CD-ROM, before CD readers were standard on PC’s or windowed operating systems were the interface to your computer. The company was founded by Gary Kildall and Tom Rolander. It was a company of about 15 geeks - and I mean that with every connotation of the term.

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