5 things I wish someone told me when I first started with Nathan Wenzel, CEO of SimpleLegal

5 Things I Wish Someone Told Me When I First Started

I had the pleasure to interview Nathan Wenzel. Nathan took a more methodical and consultative approach to founding his start-up compared to others. SimpleLegal is helping Fortune 500 and blue chip Silicon Valley start-ups completely re-think their approach to legal operations — they’re the Salesforce of Legal and giving a modernized, data-driven approach to this corner of the C-suite.

Thank you so much for joining us. What is your “backstory”?

Two massive economic meltdowns shaped my view of what it means to run a business. I started my career in 1999 at the height of the dot-com boom, then had to survive the 2008 Great Recession while running our first company.

Growing up, my family had an Apple ][ + in the house, so I was always around technology. But I didn’t graduate from school with a computer science degree and head straight into the startup world. I graduated with a finance degree from Arizona State University in 1999 as the dot-com boom was in full-tilt crazy mode. I started in a finance role at the Phoenix office of a 2,000-person company that grew to 4,000 people and got acquired over the following year. A year after that, the combined company collapsed from 10,000 people to zero.

At that first company, the average employee age was about 25. From there, I landed at a shipping company where the average tenure was about 25. Great people in both places, but massively different cultures. I met my cofounder through that job and we started a data analytics company working primarily with legal departments at large financial institutions, where over the next decade we built a great team and bootstrapped our way to 7-figure revenues. Then the 2008 Great Recession took quite a toll on our customers. We managed to sell our way through it mostly unharmed, but we knew we wanted out of professional services and into software.

In 2013 we applied to Y Combinator (YC), seeing it as a great way to help us think about how to switch from services to software. But, we didn’t think we had a chance of actually getting in with a legal technology company. At the time, YC was more consumer and tech focused. We were pretty shocked to get accepted alongside some of the smartest and most driven people I have ever met. That is when we moved from legal data analytics to launch SimpleLegal as a software company.

Which person or which company do you most admire and why?

There are so many people to learn from, it would be a mistake to say there is only one person I admire. But, if I look back early in my career, my first boss, Jim Duckett, set an example of what it meant to never give up. He didn’t have any special advantages handed to him. He just kept going forward. He did it with a positive attitude and always looked for ways to pull others up with him. I was incredibly fortunate to have that example to learn from when I started my career.

How have you used your success to bring goodness to the world?

Being second-time founders with a few more years of experience (and, ok, being older) than the average tech founder gives us some additional perspective on what bringing goodness to the world means. Over the decade running our consulting company, we watched as several of our employees got married, bought their first home, had children, and took amazing trips to far off places. It was great to see the success of our company enable people to live a fulfilling life. We’re fortunate now that we get to see that again at SimpleLegal as we continue to grow the team. We set out to be a place where people have an impact and create value for customers.

What are your “5 things I wish someone told me when I first started” and why?

1. Starting a company really is one of the hardest things you can choose to do to yourself. To add to the misery, the “hard part” of starting a company will last a lot longer than you might think. The Airbnb story of their first 1,000 days is incredible. I got lucky by having the best possible cofounder anyone could ever hope for and by having a supportive family who basically gave up 100% of their weekends for nearly a year so I could focus on launching the company.

2. About 99% of what you read around early-stage startups who are “crushing it” is actually false. Founders have a great reality distortion field. It’s practically a requirement to make it through the tough times. But, comparing yourself to what you read in the tech press is a losing battle against a fictional opponent. Save yourself the mental anguish – don’t create unrealistic comparisons for yourself.

3. Venture investors want to hear crazy ideas, not pragmatic plans. When I first pitched investors, I was talking about how we would add customers slowly at first, because that’s how enterprise SaaS works. Honesty is always a good policy. But those pitches did not go well. Harry Stebbings once correctly called me a rule follower.

4. As a company grows from one stage to the next, you have to throw out what worked and change your mindset to the next mode for success. For the early team, optimize for ability to get things done, not any specific experience. Very few people can actually push a task over the finish line. But, once you hit initial traction, you have to switch to optimizing for hiring people who can build systems. Through that transition, adding bodies without systems and process only creates more chaos.

5. The #1 requirement to be successful in your startup is to never stop. Just being sufficiently determined by itself is almost enough to make any decent idea work. Believing in that truth will make the tough days (and weeks and months) a little less painful.

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