We were lucky to catch up with Jameson Pitts recently and have shared our conversation below.

Jameson, looking forward to hearing all of your stories today. One of our favorite things to brainstorm about with friends who’ve built something entrepreneurial is what they would do differently if they were to start over today. Surely, there are things you’ve learned that would allow you to do it over faster, more efficiently. We’d love to hear how you would go about setting things up if you were starting over today, knowing everything that you already know.

I would do it all painfully the same. Not because I did everything right, but precisely the opposite. No matter what advice you are given, by the right person at the right time, no matter how smart you are or how trained or educated you are, as an entrepreneur… you have to learn every lesson the hard way. It’s like before you’ve ever been on skis, before you even have your first ski lesson and your friend says to you, “Just remember it’s all in the hips.” That is good advice, but that’s not meaningful advice. It doesn’t mean anything to you, the novice, the beginner. You can’t feel or apply that advice until much later. Until you have rocketed down the hill, shaking through your pizza and slamming into the side of a lift line a few times before you figure out… It’s that little twitch, that little skate of the skis over the snow, bringing the tails around behind you, all rotated by the hips, that makes all the difference. Likewise, there is no shortage of advice you will be given as an entrepreneur. Little aphorisms like “Remember, pay yourself first.” Even though it sounds strange, selfish even, that is actually good advice. But again, it doesn’t mean anything to you. When you as a business owner are looking at payroll and stretching to make it, and you make that first choice to dip into your savings—and you feel like you’re doing the right thing. And you know, that payroll you should do that because that’s the right thing to do as the owner of the business, those people worked for their pay, but actually the tough management call is to cut costs or to shake up whatever you are selling to try and find a better fit, or to raise your prices. Paying yourself last is permitting you to operate blind, to not pull the levers of the business that are your responsibility to pull. But you need a real emotional connection to that decision to understand it, you have to have made that mistake before for it to have meaning. Likewise, when to let someone go? Had to learn it the hard way. There is no way to learn what it feels like to fire someone from a book or a mentor. There is no substitute for the tinny taste of blood—but the lesson is that sometimes it’s compassionate. Keeping someone in a role where they continuously fail to thrive is no kind of life for them and a disservice to the rest of your team to whom your responsibility lies. But I had to feel both sides of this, and make the mistake in each direction, to be able to make these decisions effectively.

Jameson, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

About a decade ago I started a creative studio called Sangfroid. We’re a shop of about 10 people in Austin, Texas. We make brands and websites and take them to market. We have a penchant for unconventional, untraditional and unforgiving design. We love to work with bold creators, personalities, innovators, startups, weirdos, etc.
We are what might happen if an old-school mad men advertising agency were tuned for a new school of design and product and growth marketing. We obsess over the media on which we appear and the meaning of the creative and message we deliver.

Do you have any stories of times when you almost missed payroll or any other near death experiences for your business?

Every business has them! Most succumb to them. In fact, this is the loudest advice I have heard from my mentors over the years. If something tough happened, one would say to me simply: Stay in business as long as you can. Another put it this way: Rule number one is don’t run out of money. Rule number two is, see rule number one. And a partner of mine said, Don’t worry, every successful business has on average 3 WFIOs, even the ones that go public. (We’re F****d It’s Over—There’s a famous article on a16z about this) In the early days of the business, the first couple employees, I once made payroll by feeding the crumpled dollar bills in my pocket into the ATM. To the dollar. Every payroll is something of a miracle for a small business—most do not make it past 2-3 years of payrolls.

Have any books or other resources had a big impact on you?

Two come to mind—first is It Doesn’t Have to Be Crazy at Work, by the Basecamp guys. This book is radical, and some of the advice is so extreme it’s difficult to apply, but the spirit is true. Little things like chat (Slack, Teams etc) really suck. They do not really make us more effective, and rejecting some of this generation of knowledge workers’ false sense of urgency, always connectedness, is actually a kind of super power. I recently wrote about my own view of organizational effectiveness here: https://www.sangfroidstudio.com/blog/principles-for-effective-productivity

Second, and more importantly, is Play Bigger. This is the definitive book on Category Creation. What do our unicorns darlings like Airbnb, Uber, Amazon have in common? They are kings of their categories, and they won those categories because they created them, so they always had the best chance. This is “preparing the soil for planting,” and has dramatically changed how I see marketing. Read my book report here: https://www.sangfroidstudio.com/blog/play-bigger

Contact Info:

• Website: https://jamesonpitts.com/
• Linkedin: https://www.linkedin.com/in/jameson-pitts/