What It Takes To Be A Successful Serial Entrepreneur by Tom Chavez

When I think of the attributes of a successful serial entrepreneur, grit, organized thinking, humility, and raw intellectual clock speed typically come to mind. What I don’t typically think of is the ability to lob a liquor miniature with pinpoint accuracy across an auditorium. But last month at my startup studio’s annual event, witnessing Seamus Blackley, co-creator of the Xbox and legendary video game designer, send an airline bottle of Malibu whizzing into the waiting hands of audience members as a ‘thanks’ for asking an interesting question had me question my priors and ask: maybe a good pairing to founder soft skills is hard alcohol.

Seamus is an old friend – someone I was lucky to know long before he was building and creating alongside Stephen Spielberg and Bill Gates. More than that, over the years, I’ve had the privilege of listening to Seamus’s valuable insights and personal stories about innovation, entrepreneurship, and lessons he’s learned, which got me thinking about three of his most game-changing pieces of advice – and how they’ve applied to my life and how they should apply to yours.

Your environment makes all the difference.

As accomplished as Seamus is, he’s also had his share of flops. Relatable, right?

The story goes like this: once, early in his career, Seamus was responsible for one of the biggest flops in the gaming industry, Jurassic Park Trespasser. Now, that same game has become a cult classic, with its physics engine influencing much larger blockbusters that came after it. But what went wrong? As Seamus described, the environment he was in was just not supportive – he was a creative in a room full of accountants, and he got as close as he could to realizing his vision but ultimately had to ship something half-baked. In hindsight, he should have taken his team of crazy dreamers somewhere where they could have followed through.

Builders are a different breed. I so often think about the divide between craft and critique – the ability to create versus the ability to only poke and nudge. Surrounded by engineers, we’re literally building the impossible – making things appear out of numbers and code. It’s the ultimate creative act. And, of course, in business, the bean counters need to come out of the woodwork at some point – but they can’t swoop in like corporate antibodies to kill innovation wherever it’s happening.

Cultivating the right environment with the right balance of creativity and discipline, dreaming and bean-counting, is key.

Curiosity outweighs experience. Every time.

Look, I’m all for accomplishments and credentials – to a point. It was comforting to VCs who backed me in the past to see my degrees from Cambridge and Palo Alto on my CV. There are many smart people that fit a profile like that, but 95% of them aren’t built for early-stage company-building.

Seamus shared a great story: he was comparing two candidates for a single role. The first had 15 years of experience in the field, multiple stints at the big-name companies that specialize in what Seamus was hiring for. The second had none of that. What he did have was a bunch of experience tinkering on that exact problem and skillset in his garage in his spare time.

Seamus made the mistake of hiring the first – who quickly flamed out when his specialized experience hit the brick wall of going from 0 to 1 in an early-stage company. So Seamus hired the second candidate, the tinkerer and passionate hobbyist, and that individual ended up revolutionizing their system and growing to be in charge of it.

Curiosity trumps experience every time. It’s also a great filter for those with composure under pressure because solving hard problems creatively is what fires them up. It’s the ones who question the status quo and chase their curiosity that achieve remarkable results – like Seamus himself.

It’s all a mental game. Hold fast.

Of course, none of this is easy. Like I say on my podcast, building a company from scratch is soul-sucking and pride-swallowing hard – but it’s the best thing ever. It may be fun, but it’s always a challenge.

Seamus shared a bit about his personal struggles and the toll that entrepreneurship can take. This is pain that’s deeper than anything physical: it takes a mental toll on the uninitiated, and every setback is a psychological struggle to not lose hope and maintain self-esteem.

Starting and running a company – especially the first time – pushes you to your limit. Setbacks will never kill you off if you keep your long-term vision in place. I mentioned Seamus’ famous failure – Jurassic Park Trespasser – that today is a cult classic in the annals of PC game nerds. But from that failure, Seamus went to Microsoft and conceived and successfully pitched the concept of the Xbox. The common thread? Seamus was laser-focused on the intersection of, in his words, “creativity and technology.” He pushed the envelope with Trespasser and its attempt to tell a Spielbergian story with the most advanced physics system PC gamers had ever seen. It flopped. The only natural next step was to go bigger and build an entirely new device that combined creativity and technology into a winning platform for video games. Seamus conceived of Xbox, pitched it to Bill Gates, and the rest is history.

And lastly, may we all learn from one of Seamus’s pieces of wisdom: “On your deathbed, you’re not going to lament that you didn’t spend enough time being afraid. You’re going to lament all of the things you didn’t do because you were afraid. So why not remember that now? That’s it.

Hold fast.

Source: entrepreneur.com

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