Against-the-Grain Advice for First-Time Founders

This article was published in the Fall 2020 issue

by Matthew Roberts, CEO, Savvi Legal

"The first is the hardest" has been true for a lot of firsts in my life. Dealing with my first “heartbreak” at 16 and landing my first kiss at 17 (I know I got the order wrong). Initiating my first missionary street contact at 19. Breaking my first horse. Rowing through my first class 4 rapid. The list goes on.  Founding Savvi Legal has, in many ways, captured the crazy emotions from all of the other hard firsts in my life, and repackaged them into one wild ride. It became more challenging than I had ever imagined when I decided to quit my job and dive into the deep end. I especially failed to grasp the challenges that apply uniquely to first-time founders. Rather than giving aspiring founders a feel-good article with buzzy catchphrases and feel-good axioms (your social feeds are full of them), I thought I’d share some against-the-grain advice and perspective as a first-time founder who is still in the thick of it.

Don’t hide your failures.

"It is not the critic who counts;..The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming;..who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly..." -Theodore Roosevelt

Being a first-time founder has been an extremely rewarding, but also lonely and humbling journey. The loneliness that I’ve felt has come from feeling the pressure to maintain a certain facade of success, sometimes referred to as “fake it til you make it”. This dynamic is the reason behind seemingly “overnight success” stories, along with the overnight failures that catch us by surprise. I’m not saying to throw best PR practices out the window, but I see too many founders (especially us first-timers) take this mindset to the extreme. I’ve learned that by increasing accountability and transparency about failings and mistakes, I’ve been able to build more trust, loyalty, and commitment with my team, advisors, and customers. One of the best decisions I made early on was joining a mastermind founder group that has since evolved into a rapidly growing founder community called FounderPod ( Having a group of peers and a safe space to open-up about my failures, challenges, and personal struggles has made all the difference for my mental health and helped me realize that I’m not alone.

Go all in when you’re young and poor(ish)

I have a lot of really talented friends who can't wait to be founders when they grow up.  The problem is that the reasons to delay start to stack up (think college debt, mortgages, lifestyle expectations, children, laziness, health risks, church service, death) I also see other founder hopefuls waiting for their moonlight project to magically grow wings. While it can make sense to phase some founding team members into full-time roles, I rarely see first-time founders get enough traction with their startup to either raise money or launch a sellable product without at least one co-founder “burning the ships” and taking on the risk as a full-time founder.

In my case, I was ready to make the leap as soon as I had developed a foundational set of experiences and skills to leverage for my own venture, along with enough savings for a two-year runway (I recommend starting while you’re still poorish, not broke). My brother and co-founder, Dan Roberts was much farther along in his family journey, but was looking for opportunities to jump in as soon as he had paid off his law school student loans. After several months working to validate our idea for re-imagining the legal experience for both founders and their attorneys, Dan and I both decided to commit to the project. He immediately put in the seed capital to get us to an MVP, and within 6 months had quit his law firm job, sold his house in Texas, moved his family of 6 to a little farm in Utah, and had joined me in the startup grind. Not a day goes by that I don't feel grateful to him and his wife for taking the plunge into the valley of the shadow of startup-life and yoking up with me to pull the Savvi wagon towards the promised land of growth and profitability. Take our word for it. If you’re going to found a startup, it’s only going to get harder the longer you wait.

Be lean without cutting corners

One of the nicest things about lean startup theory is that most founders don't have any other choice but to be lean. The problem is when the lean mindset turns into a growing pile of rotting skeletons that will inevitably come back to haunt you. Take startup legal work as an example. Yes, this is a convenient example given that Savvi is built for this, but I have also developed a firm conviction after seeing countless startups pay the price for cutting legal corners early on. Here are just a few reasons why you shouldn’t neglect your legal agreements and filings as a founder:

  • Protect relationships and avoid lawsuits
  • Protect your intellectual property
  • Save time and fees during due diligence
  • Minimize taxes and stay compliant

There are a whole host of things you’ll need to know in order to navigate the treacherous waters of founding a startup.  The good news is that if you use the right tools and service providers for your back-office needs (i.e., legal, tax, and accounting), then you can have the peace of mind that your ducks are in a row, so you can focus your time and energy on more strategic and growth-related initiatives.

I hope to see you in the arena with me soon.

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*Read the latest issue of Silicon Slopes Magazine, Fall 2020GhostMagazine-cover---Summer-2020-3
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