If You Don't Break the Rules 👊 You'll Never Have a Breakthrough Business


ISSUE #52

Welcome to the Forward Obsessed Founder, my newsletter with insights, awesome tools, and real-world advice to grow your business and career.

GO FORWARD THOUGHT OF THE WEEK ➡️

If You Don’t Break the Rules 👊 You’ll Never Have a Breakthrough Business

The other day, I was driving down the street and noticed cars flying by me.

How could that be? I drive a rocket ship on wheels. (Not a flex… well, OK, a little flex.)

Answer: I was following the rules and going the speed limit.

Which is a good thing in general society… but what about business?

That's when it hit me:

Great founders break the rules.

I’m not talking about legally binding rules. (Although plenty of super successful business owners bend them — not that I’m advocating for that…)

I’m talking “business rules.”

Sure, there are plenty of rules of thumb.

Unwritten rules.

Rules of engagement written by someone else for something that predated you or doesn’t apply to your business.

Norms, if you will.

If you want to break through, sometimes you have to break away. That’s why rule breakers rules.

ThoughtSpot, a Startup Rule Breaker

Think about all the “rules” for being a startup founder:

  • You’ve got to make fast decisions or die, so no more than two cofounders.
  • Failing fast and often is the secret to your success.
  • Whip out your MVP so you can get funding, stat.
  • Established leadership is catnip for investors, so go with proven people.
  • Founders and company leaders need to stick to their defined roles.

When you read that list, did you think, “Yup, those are good rules”?

If so, feel free to stop reading here. You’re not truly forward obsessed, and what comes next might upset or offend you.

But if you’re like, “Hmmm… that’s all conventional wisdom based on someone else’s playbook. And none of that is a hard and fast rule by any stretch,” then you’re like ThoughtSpot’s cofounder, Ajeet Singh.

Singh is the brains behind the innovative AI-driven analytics platform, which was launched with seven — count ’em, 7 — founding partners. That was his first big idea because he and his first cofounder, Amit Prakash, decided that the only way to accomplish their ambitious, visionary goals was to entice the best of the best.

While their expertise was in enterprise software and machine learning, Singh and Prakash realized they needed a diverse leadership team of industry leaders in key areas, including search infrastructure, cluster management, and business intelligence.

So, how do you get top talent to join your nascent venture?

In Singh’s case, he offered them ThoughtSpot ownership and a cofounder title. After interviewing around 60 people in 2012, he found five ideal experts to join him and Prakash as founders.

Instead of being satisfied with jamming out an MVP and screwing up as much as possible, they spent the first three years building a full-on product with robust features ready upon launch.

Along the way, the cofounders were flexible with their roles and responsibilities, adapting to whatever was best for the company’s growth.

Their unique, collaborative approach paid off big time — they raised $663.7M over 12 rounds.

Today, ThoughtSpot has exceeded 40% year-over-year SaaS growth and had a $4.2B valuation as of its Series F funding in 2021. (Extrapolate from there 😉)

The only rule you should take away from the ThoughtSpot story is to stop following rules.

After all, every entrepreneurial venture starts with an “aha moment.” And why do we say “Aha!”?

Because it’s something that’s never existed before.

In other words, every aha moment springs from a broken rule.

So what’s stopping you?

Always here to help 🙌

Pete Sena


Tool of the Week 🧰:
THE IDEA DOJO: Your 24/7/365 creative sparring partner

The Matrix changed my life for so many reasons.

One scene that always comes back to me is the iconic dojo fight when Neo wakes up after having hours and hours of information uploaded into his brain and says, "I know Kung Fu."

Morpheus responds, "Show me."

Then, they have an epic fight scene, and Neo has all the power and the magic at his fingertips.

That happens to us entrepreneurs sometimes. Some of the best moments of my career happened when I got into the ring, so to speak, to riff with a great creative sparring partner, stacking, building, and shaping ideas.

But let's be real: it's rare for things to come together that way. Ideas hit us at random times and in random places. You can’t always wait for your team to kick some a$$.

So I dug in with my squad at The Resonance and teamed up with a PhD in machine learning to start building a 24/7/365 creative sparring partner I call THE IDEA DOJO.

If you need this, hit reply and lemme know. I’m trying to figure out if I’m gonna release it and am in talks with some large brands and agencies right now.


Thanks so much for reading this edition of The Forward Obsessed Founder — you can also check out this issue on the web [Link].

Spread the word and grow my mission together

Three ways I can help make your CFO and board love you right now:

  • Help you discover new revenue streams for your business that are hiding in plain sight.
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Please take a second and hit the FWD button ▶️, to share this email with your favorite growth-obsessed peer. I want to inspire 1 million awesome minds like you.

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Pete Sena

I help founders design demand & business growth, and visionary brands create what's next. Startup Advisor. Founder @digitalsurgeons

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