What if the Founder’s personality is a startups liability?

TL;DR: “What do we do if we suspect our own personalities might be a problem in our startup? How do we know if it’s even something to dig into? And if we do find out we’re the problem, what do we do about it?

During the early days of my first startup I stumbled upon a huge liability that was killing us quickly — me.

What’s funny is no one else needed to have this discovery. The rest of the organization had figured out long ago that I was immature, combative, prone to anxious tirades, and generally a pain in the ass to work with. And looking back, I’m probably being kind.

As a Founder (and CEO), every single one of those idiosyncrasies becomes amplified a hundred-fold because my liabilities to the organization become rooted in every decision we make, every interaction we have, and the entire morale of the company.

If we don’t exercise some serious self realization — and do it quickly — we may be creating one of the biggest hurdles our organization has to overcome.

Today’s Advice Sponsored by Divvy

It Starts With Strong Commitments

The foundation for having a startup that supports our dream lifestyles is making really strong commitments to those lifestyle choices. For example, if we’re parents and we want to make sure we never miss our kid’s soccer game, we have to publicly make that commitment and stick to it.

Sometimes just announcing those commitments is a great way to get the ball rolling. When we launched Startups.com we had all just had our first kids, so we made a proclamation that we would never let the business get in the way of our families. 8 years later we’ve never broken that promise, largely because it was committed to very publicly, so we could all actively support it.

Take Baby Steps — Then Commit

Where we blow this up as Founders is when we try to take it too far too fast. No, we probably can’t work from a beach in Fiji for 6 months out of the year (yet). But can we try working remotely for a solid week? A big part of shifting our workflow and culture is just making small, consistent steps toward adjusting the company to fit our goals.

When we wanted to create more flexibility at Startups.com, we started by just trying one Wednesday where we could work from home. It was easy to try and easy to reverse if it didn’t work. Now, over 200 people work remotely and we’re more efficient than ever. Those baby steps are what made it possible.

Bring Personal Goals Into Corporate Planning

All too often we separate our “startup goals” from our “personal goals” as if they’re not allowed to intermingle. But really, our startups often ARE our lives, so separating the goals and activities doesn’t make any sense.

What’s worked well for us at Startups.com is that we sync our personal goals first (commitment to our families, free time to pursue interests, how we want to help people) and then figure out how our business can support those goals. We make daily decisions based on that compass, and our lives reflect that.

Lifestyle Design Isn’t a Myth

There’s very little preventing us from designing our startups around our life goals. It starts with us being very clear about what we want to achieve and then taking clear, small steps toward those outcomes.

Life is too short. If we’re going to create something beautiful in the world with our startup, there’s no reason we can’t build a beautiful lifestyle in the process.

“How do I know if I’m the liability?”

That’s the hard part. As Founders, we’re often the last to know because our worlds aren’t entirely set up for total honesty. It requires some actual digging, which, to be fair, is a scary exploration. It helps to have a friend, mentor, co-worker, or spouse that we can trust enough to shoot us straight.

Finding an honest person is the easy part though. Asking the right questions is the hard part. If we use polarizing queries like, “Do people think I’m a total jerk?” we’re going to invite potentially kinder responses in fear of offending us. But something more aspirational like, “Where should I be spending time improving myself?” could really open up some helpful insights.

Trust me, when we are the liability as Founders, it doesn’t take a ton of digging to get some honest responses. Not asking and digging is the real problem.

“What do I do if I’m the liability?”

Get in front of it. Confront the people that we’ve offended or pushed away. In this day and age, fundamental honesty and contrition are a rare commodity. When I pulled people aside and started admitting, “Hey I didn’t realize what a jerk I sounded like in that last meeting…” it blew people away.

The truth is, I didn’t want to be a jerk, and I definitely didn’t want to be a liability. The reality is we can’t prevent ourselves from becoming our worst liability unless we take the time to assess ourselves fairly — and more importantly, do something about it.

8000% growth and an ice cream cone: The origin story of Divvy

Once upon a time, CEO and co-founder of Divvy, Blake Murray, was in a parenting pinch.

He wanted to give his kids money to spend on things like ice cream, but the thought of handing a child a credit card scared the sprinkles off him.

Blake wanted a card without a balance that would let him fund and monitor his kids’ spending — without worrying about it falling into the wrong hands.

And like that, Divvy was born.

Since January 2018, the company’s grown more than 8000%, secured $254m in funding, and has thousands of clients.


By rethinking the corporate card

Divvy distributes both virtual and physical corporate cards, so every employee — from the intern up to the CEO — can have their own with the funds they need to do their jobs.

And here’s the kicker: you control exactly how they spend. 

Once you give the thumbs-up, meals, software, and travel (which they make easier than ever, thanks to the seamless new Divvy Travel app) are all automatically categorized and expensed.

That means no end-of-month receipt scramble, no missing visibility, and no scouring through emails trying to figure out which airline site Bob from accounting booked through this time.

Oh, and did we mention it’s free? Divvy makes their living off virtual card transaction fees, so you don’t pay an extra penny.

Don’t band-aid your budget problem — solve it. Decision makers get $100 to demo Divvy.


In Case You Missed It

The Cost of Toxic Employees (podcast). We all know the value of having a star player on our team. But what about the opposite? Wil and Ryan discuss how to identify and handle toxic teammates before their impact spreads across the organization.

How Does a Founder Get Fired? Fired as the Founder — totally a dream, or a nightmare come true?

Fighting Cynicism In Company Culture. What are the root causes of cynicism? And how we keep it from contaminating our company?