A Repeat Founder's Ten Self-Commandments
Sharing so you can avoid the pain--and I drill them into my own thick head
I will be the guest speaker at my friend Adam’s team event in about an hour. He leads the sales organization at a fast-growing marketing technology company and asked me to share some of my early startup experiences to help inspire his team. I’m looking forward to sharing stories “live” for a change.
As regular readers of this space know, I’ve got a lot of stories to share! Across just my startup work, I count seven specific new business ideas that I’ve put real work into. Throw in a few board roles, angel investments, and mentoring, and I’ve been directly involved with a couple dozen more companies.
I sat down and my desk and started with the thought: What simple list of lessons do I wish my “future self” could go back and time and deliver to me to improve my odds of success? Within minutes I jotted off a list of 10 Startup Self-Commandments that included a combination of mistakes to avoid and success strategies that worked well.
Whether you’re considering starting or joining a startup, a repeat founder, or just looking for how to get the entrepreneurship mentality, I think you’ll find value from lessons I’ve learned the hard way. Here goes…in no particular order:
Don’t Do Free Work - You are building a product or service that adds value to customers’ lives. And you deserve payment for delivering that value. You’ll land customer logos with free offers, but they won’t care much about the output because they are not invested. You won’t serve them well because you’re not getting paid. Plus, getting paid for your work is the ultimate proof that you’ve created something that has the potential to be a real business.
Beware Taking Investor Money - Last week, I wrote about some of the downsides of raising money from investors, but there are many more. It’s a huge time investment, it leads you to make poor business decisions, and there’s a good chance you’ll have a mismatch in character, power, and interests. You’re literally selling your company—inviting in bosses and reducing your ownership value. Ignore the hype and see if you can build something of value with as little outside investment as possible.
Don’t Participate in Pitch Contests - It’s so tempting…and such a complete waste of time and emotional energy. You’re just someone’s content slot. The judges are not buyers. Corporate business teams barely care. If you solve a real pain point for your customers, you’ll have no problem getting in front of them and making a sale. I've fallen for this trap countless times and gotten near-zero value. Never again. Really.
Don’t Work with Jerk Clients - Even when your business is struggling this is rarely worth the effort. The mental cost is too high for you and your team. Life is short. Reality check: If your business can’t survive without a few shitty clients, you don’t deserve to be in business.
Only Hire When It Hurts - Avoid the fundraising traps and get closer to the sweet nectar of profitability by being incredibly careful with hiring. Do the grunt work yourself to learn directly and build processes that can be turned over to software or freelance help. Hiring not only adds direct cost, but cultural troubles, too. When you’re at risk of missing revenue because of a lack of people, that’s the “hurt” that triggers hiring. And when you do hire, lean toward dependable, self-motivated people.
Expect to Pivot - Know going into your startup that no “great idea” survives first contact with the customer. You’ll be doing much listening and learning in your early pitches and product development. Your pitch deck will change daily. This is why it’s best to keep your day job as long as possible, do things “by hand” before building software, and not spend or raise much money.
Find Existing Budget - Whether selling to individual or enterprise customers, it’s incredibly hard to get people to pay for something “new.” It adds a ton of risk and reasons to say “no.” With enterprise, in particular, these times of profit pressure and many approval stages are maddening. Your only way to win is to find buyers with searing pain and a budget approved to eliminate it.
Process is King - Your objective is to create a machine that prints money. A machine works in a simple, repeatable way. That’s process—a way of efficiently doing the work. Make decisions and create processes around them so you and your team don’t have to “think” as much. Examples include a pricing formula for your sales team, a product roadmap and sprint system, and a hiring playbook.
Create a High-Performing Organization - People power your company. People will reach the stars when you create a company they love to work at. It’s your job to give them: (1) Ownership - let the people doing the work make decisions; (2) Transparency - always share what’s happening with the business and why any change is made; (3) Values - create an expectation for how people should work together and use this as the focus of hiring decisions; and (4) Vision - know and share where the company is headed, which will attract and energize people that like the direction.
Have Fun in the Process - Startups, business, and life itself is a game—and any game we play should be fun. A playful approach to work is positively contagious to everyone inside your business and with your outside clients and partners. Lead by example by creating smiles among your team—and never take yourself too seriously.
When Moses came down with his Ten Commandments, his “team” didn’t immediately embrace them. It took 40 years for his followers to internalize the lessons—often by violating them and suffering the consequences. I, too, sometimes violate these very rules that I preach to others.
But with each plate appearance, my mental muscle memory improves, and I’m less likely to strike out. In fact, writing and sharing with others here helps me stay “in practice.” Thank you, dear reader, for giving me an excuse to keep my skills sharp. And I hope you’ll do the same for others as you build your own hard-earned success lessons.
Bob Gilbreath is a 2x-exit entrepreneur and co-founder of Hearty, a curated matchmaking service that combines top software developers with early-stage, venture-backed startups.