You Ask, I Answer: The Most Important Business Decision?

Conor asks, “It would be great to hear about an important business decision you’ve made in your career – the pre-considerations, your thought process, the steps you took to put the decision into action and the key takeaways.”

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Machine-Generated Transcript

What follows is an AI-generated transcript. The transcript may contain errors and is not a substitute for watching the video.

Christopher Penn 0:13

Probably the most impactful decision I’ve ever had to make is the founding of Trust Insights.

My business partner, and I, Katie, we work together at a PR agency.

Katie was actually my direct report at the time.

And we saw that the agency we worked at at the time was going in a different direction than we wanted to.

It was focused on objectors we didn’t agree with.

We found ourselves taking on clients that we had moral objections to, we thought, but some of those clients, their businesses, fundamentally made the world a worse place rather than a better place.

And so a combination of data points that suggested that the business was going in the wrong direction, plus some emotional points of view told us it was time to take the big leap.

One of the big considerations to that while there were several.

One was, did we have something viable to offer the world that would be worth paying for and the fact that the team that we ran was the most profitable team in the agency had three of the five largest clients and represented? Probably 20% of the entire company’s revenue told us yeah, there’s a way to build our business.

So that we could take the things we learned at the agency, but recast them to be our Central Focus, focus on management, consulting, data science, machine learning, artificial intelligence, analytics, and leave behind the awkward sort of juxtaposition of a profession that fundamentally is not data driven, trying to make that mesh with data driven processes.

So that was the decision itself.

Some of the considerations that went into it, were things like, did we have an audience? Now, for the last, at the time, it was 10 years, when we were when we were starting to make these decisions.

I had been building my personal brand, my personal audience of people who went to my website, sign up for my newsletter and stuff.

And at the time, we launched, about, like, 50,000 subscribers to my newsletter, we felt like, Okay, that’s enough of a pool, that when we make the announcement, there’ll be enough people interested in our products and services that we could survive.

We looked at our personal savings, our personal finances, we looked at potential projected revenues and things and decided, yeah, it would be tough for a couple of years, for sure.

That’d be tight for a couple years.

But there was enough there enough momentum already in place, that it wouldn’t be starting from ground zero, it wouldn’t be starting with nothing, it’d be starting with the ability to bootstrap.

One of the things that went that happened early on was, as we were forming the ideas of the company, we’re trying to figure out how to do our funding.

And we actually pitched investors early on for the company, and found that the investment community itself was very reticent to invest in a services focused business, they were looking for product focused businesses, because it’d be easier to invest and see returns faster, flip them faster.

And two of the nine investors we pitched were absolutely morally reprehensible people, it turns out, they told us to our faces, which credit to them for being honest, I suppose that they would not invest in a business with a CEO was female, which was just offensive.

And so that, that changed how we ran the business and how we’re going to fund it to basically being a bootstrap business where we would not accept outside funding, Katie, and I would retain full ownership of the business.

And that would be how we would approach things like the finances.

And so in March of 2018, we took the leap, and we we left the old company, we started we hung out a shingle, and the first year was definitely tough.

But after that, we got some momentum.

We got some focus.

We really dug into what we were good at.

And now four years later, we are a thriving, successful business.

We are we closed our first million dollars of revenue not too long ago.

We are looking to make our first annual million dollar revenue very very soon.

Which is not bad for you You know, a business with two owners and and one contract salesperson.

Christopher Penn 5:06

And the business model that we have now is part software part consulting.

And so we expect to be able to scale the software side of things, along with some training courses and things that we’re putting together to really grow the business substantially in the next couple of years.

And again, because it’s funny, those investors that declined to invest were a blessing in disguise.

Because as we grow the business to being first a seven figure business than an eight figure business, hopefully a nine figure business, we didn’t have to give up any ownership, we didn’t have to, to give away any decision making capability to other to third parties, we are accountable only to ourselves.

And we get to keep the the the profits, which is also really nice.

So in some ways, those those investors who said no, really were a blessing in disguise, it really were.

And so the key takeaways for a big decision is you’ve got to do an inventory, what do you have? What, what data do you need to make a decision? Use your Eisenhower matrix or your Franklin index, whatever methodology take into account the emotions, you know, as I said, one of the big challenges early on, was dealing with taking on clients that you know, at the old at the old company that we found morally objectionable.

When you start a new business, we codified it’s funny, we codified all the things that we didn’t like, in the old company.

We said we don’t like this, we don’t like this, we don’t like this, then we took the reverse and said, Here’s what we do.

Like, here’s what we do want to do, and made that part of a corporate core values to say these are the things we stand for, and the things we won’t put up with.

Because otherwise, why bother? Right? Build a business that you want to work at because there’s a good chance especially if you’re going to be making a decision like this, that you will be working at it for a very long time.

The idea of building a business and flipping in 18 months not realistic for most people nor you know for nor for someone like me would that be personally very satisfying want to build something and grow it and watch it grow.

Your personality may differ of course.

But that’s those are kind of the the way the story unfolded.

It’s it’s still being written.

But wouldn’t change a thing.

wouldn’t change a thing.


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