Startups are hard. So why did I join one?

The data says most startups fail. Here’s why I left the cushy corporate world to join one.

I spent the last 7 years of my life at Tableau. During that time we went through hyper-growth, a stock price collapse, a return to growth, and eventually an acquisition by Salesforce. I led a large team, and our product (Tableau Online) was Tableau’s fastest growing business. 

We were supported by robust corporate infrastructure with HR, Recruiting, Operations, business rhythms, release management, and a constant cycle of "reviews" designed to move us forward and avoid missteps. And, of course, I had all the cushy benefits of a large software company (tech salary, stock grants, ESPP, 401(k), childcare, fitness, laundry…). 

By comparison, early stage startups can be a struggle! The product is, by definition, fluid. The support ecosystems are meager at best; there is a ton of self reliance, and oftentimes if you want something done, you need to do it yourself. You don’t have all the stereotypical perks of a mature tech company. So why would I choose to run towards all that by joining Plus?

What got me thinking

A few months ago, my daughter developed a new habit: every day after returning from school, she pops her head into my basement office and asks me, "Did you have fun at work today?" The first few times were easy, and I’d respond reflexively, “Sure, I had a good day today.” But the repeated questioning got me thinking. And the more she asked, the harder it got to find a positive answer. 

We’re all used to hearing some version of, "If you're not jumping out of bed to go to work, then maybe it’s time to move on..." Some of this is obviously hyperbole (all things have ups and downs, and everyone has days when you just want to hit the snooze button!). But my daughter’s questions sparked the question: Could I be having more fun?

So when the phone rang the next time, I answered. Over the next few weeks I met with Dan and Chloe, the founders of Plus. They were excited about what they were building (the easiest way to capture, see, and share up-to-date data from any source), and a few minutes into our conversation showed me a demo of what they were trying to do.

Their enthusiasm was infectious, and the demo struck a chord. I had spent the last 7 years at Tableau with a mission of, "Helping people see and understand data," and the most important words in that mission were always, "helping people". I could immediately see teams across Salesforce using Plus to reduce the grunt work of combining data from multiple sources and prepping for weekly/monthly reviews. The problem seemed worth solving, and the product seemed to be on the right path to solving it. 

But why did I ultimately decide to take the leap to join Plus, leaving behind a comfortable position (and great team!) at Tableau?

Time is precious.

We only have so much time to do something amazing with our lives. Much of corporate life is removed from where value is created, and before you know it a lot of what you're doing can only be classified as a ”BS job”. And maybe large organizations need them, and maybe that’s a good fit for some people, but it definitely wasn’t getting me out of bed in the morning!

Work on something that matters.

Just about everything in the world takes time from you (this is especially true when you have kids, by the way!). So when I find a product, idea, or tool that gives you time back, I'm an instant fan (e.g., electric cars = 15 minutes saved filling gas every week, grocery delivery = 60 minutes saved shopping every week). If your job involves regularly updating slides (or docs) by pulling data from the same set of tools, what we're building at Plus will return to you some of your precious time.

Stories for a lifetime.

I mentioned to a friend who's a VC at Madrona (one of Plus’s investors) that I was talking to Plus. And he asked me, “What do you really want to do?” The startup community is vast, with companies in different stages, and tons of excitement in different areas (low-code/no-code, Web3, crypto/DeFi, etc). I think of life as a collection of stories, and I want to add new chapters. I've already had two stories of joining a 200+ engineer, post-IPO company and helping it grow to thousands. But I've always had the bug to build something from scratch, and I’ve only ever heard company folklore about what that 0-200 journey was like. The chance to create a culture, company and have a journey of a lifetime is an opportunity I couldn’t pass up.

The learning will be epic.

Startups are brimming with possibilities and challenges (depending on your optimism, the balance between the two might be different 😉). In either case, we're going into the unknown, and I’ve always found that I learn the most when there is a chance of failure. I have been managing teams since 2005 and led some incubation (in-house startup) efforts; these always took years to get to market (and sometimes the business lost interest along the way). With a scrappy team and finite resources, we don't have that luxury. Our incubation-to-market cycle is so fast that the challenges that were highlighted to me as the top ones during interviews a few months ago are relics of history, and we're onto new ones already. Hacking, incubating, pivoting and experimenting — now that’s what gets me out of bed in the morning!

The team matters.

At a startup, there are many variables that are outside your control, but the team isn’t one of them. One of my silent mentors used to say, "If you want to go fast go alone, if you want to go far go together". During my interviews, I had a chance to meet the extended Plus team family — not just the founders, but also the team and the investors. I felt confident that at Plus I've found the right people to go together with (3 months in, I can confirm this!).

It'll be fun.

Startups are hard. And it turns out that doing hard things is fun, partly because no one else will do it, but also because of the sense of accomplishment and learning it brings. There is an edge to the daily work that's existential. It keeps you stretching, learning, and pushing the boundaries!

The risks are real.

While these arguments are great on paper, the practical considerations are real. Startups aren't for everyone. There is less order, and each day is different. You don’t have a deep bench of support functions; there are rarely precedents or templates to lean on when tackling a new problem. Hiring and building teams will be harder. You might not gel with the team (and you can’t just internally transfer to a different one). What you're building might not find a market. An incumbent might get interested in what you're doing. A pandemic might strike. The market might crash.

Yet despite these risks, I'm 3 months in and I'm jumping out of bed with more excitement than I could’ve imagined. Sure, there are challenges — sometimes completely unexpected ones! But I’m more convinced than ever that the problem we’re solving is the right one; the team is amazing (we had such a blast getting together IRL for the first time!); I’m learning more than I have in years; and I already have great stories to tell.

And when my daughter comes by my home office and asks if I had fun today, I don't have to think twice! 


If you’d like to hear more about my experience, message me on LinkedIn. And if you’re interested in joining Plus’s team, we’re hiring!