You know that old adage about learning your lesson the hard way? I learned a lot of hard lessons during my time in startups and growing companies. Thankfully, I’ve been able to channel them into a coaching business and share those insights with you here.

You can read about the first five lessons here:

At the sixth company, I learned that when the leadership team is spending all their time trying to align their values, there is little time left to do the work of the company.

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.

Recognizing that they were operating outside their field of expertise, they asked me to come on as COO. I agreed. Here was a chance to build another business.

Doing a lot and getting little done

It became clear very quickly that the founders had used up most of their resources, and part of my role became to help raise money—required, as you can imagine, for salaries, development, and marketing.

The founders were well-connected. They had claimed to have the money soft circled prior to my joining, so my task was to present a solid business plan to the donors. Of course, as I did the presentations to these prospective investors, I learned that the money from the soft circle was very soft. The investors mostly came from real estate and politics and weren’t well-versed in tech investments. The wheeling and dealing they did in the political arena didn’t translate to funding a startup.

We finally ended up raising about a half a million dollars, which was enough to build the software and keep me moving forward. This was the mid-2000’s and it still cost that much to build a dynamic, data-driven website—a fraction of the multi-millions required in the prior decade, though a far cry from the thousands it might take today. We got bids from three reputable software development firms and ultimately selected one with whom I had previously worked.

In the meantime, I told the founders that we still needed to have a plan to market it, and raise additional funds to bring on marketing professionals. I suggested hiring an experienced firm along with a consulting CMO colleague that could help run the efforts.

One of the founders suggested that we may not need help with marketing. He already had some marketing ideas. And he handed me dozens of pages that his then nine-year old son had generated, complete with colored pencil markups. I recall that one of the ideas was to partner with the Girl Scouts, who would promote the product while they were selling cookies.

I was dismayed when I realized he was entirely serious.

Middle school marketing ideas aside, I eventually convinced them to let me bring on the marketing consultant who had experience in ecommerce and was credible.

Unfortunately, the founders were difficult during the negotiations with both the development firm and the marketing consultant.

By this point, we’d spent a lot of time and money on patents, on specs, on contracts and negotiations.

What we weren’t doing was building software or a company.

Big changes are sometimes too hard

As the COO, I had power to influence the company’s path forward. I didn’t have the power to change who we were as people. My values and the founders values were not in alignment, and given our core values don’t usually change, they never would be. They were running the business not as ecommerce entrepreneurs but as lawyers, and it created an environment that was not conducive to entrepreneurship.

They had a hot-headed, litigious approach. I valued relationship building and compromise. They wanted every detail perfect before taking any action. I pushed for the nimbleness and flexibility that allows a startup to move forward. They wanted to remove all risk. I wanted to lean into it.

Their values made sense based on their backgrounds. They were patent litigators, after all. Their job was to assess and control for risk, and fight for the rights of their clients.

The problem was: those aren’t the best behaviors for a startup founder or a CEO. Founders need to see the possibilities, accept the risks, take action, learn from their mistakes, let the little things go, and iterate as necessary.

In 2017, I wrote “An Experienced Startup Founder Learns Some New Lessons,” about my 8th startup, IntroNet. The third lesson in the piece was that the biggest gains come from taking the biggest risks.

I couldn’t generate action because I was constantly trying to build consensus and negotiate. The lack of alignment in our values meant we couldn’t get any work done.

Some things never change

We parted ways after a year.

Ultimately, the software never got built. The startup ended up in federal court litigating a suit against the software development firm. It cost several years, a half million dollars, and lots of frustrations and negotiations, for a clever service that consumers never had the chance to use.

The company no longer exists.

In Lesson #3, I wrote about what could be accomplished when you build your team around a thoughtful set of core values. In Lesson #5, I shared how two leaders with half the skills aren’t equivalent to one with all of them. In 2015, I wrote about integrity, judging values through behaviors rather than words. In a way, this lesson is a combination of all three.

I’m usually pretty good at learning from my mistakes, and provide coaching and accountability to help others to do the same. This is why I document these lessons. It’s when you make new mistakes that you know you’re growing. In this case, had I connected the combination of past lessons, I would have known at the start how this would end.

And what’s with lawyers?

For what it’s worth, when I first wrote about my experience with this company, my lesson was going to be that “lawyers make the worst cofounders.” Some of my best friends are lawyers, so don’t get me wrong. In fact, Trajectify’s writer is a former lawyer. Clearly, we tweaked it to be more politically correct. (This would be a good time to share a lawyer joke, but how many lawyer jokes are there, anyway? Only three. The rest are true stories.)

Final thoughts

There’s a bit of conventional wisdom that suggests you shouldn’t get into a romantic relationship with someone in the hopes that they’ll change. The same is true for business dealings.

Linking up with founders whose values don’t align with yours is going to be a fruitless and frustrating endeavor 99% of the time. Their values won’t change, and neither will yours.

While real benefit can be found from working with someone who has a complementary skillset or is detail oriented while you’re a big picture thinker, those relationships have to be built on a set of shared values. Spending all your time negotiating internally will limit your ability to take action in the direction of your goals.

Lack of values alignment is relatively common in companies large and small—perhaps not to the extent I’ve described. Misalignments can develop over time and get in the way of forward progress. An organizational assessment is the best way to identify areas for improvement and develop a plan to get back on course. Learn more.