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Bootstrapped Giants

The ONLY Trait I Hire For...

Published 3 months ago • 5 min read

About 6 months into starting Gateway X, I got the call every entrepreneur dreams of… David Rabie, the Founder/CEO of Tovala (smart oven/food subscription biz) was an Ampush client, friend, and let me invest in his company.

“Jesse, my first engineer… a DREAM first engineer is starting to look around after 5 years. We are 400+ people and he’s not having fun anymore.”

I felt my body tingle. After a few meetings, I hired Adam Brakhane (now Gateway X’s CTO). Within months of him joining, we launched Kahani, a SaaS startup he built from scratch. Within a year of him joining, we raised over $3M.

David wasn’t kidding. Not only could Adam build anything, but he has incredibly strong judgment and logical reasoning. He’s fast. He cares deeply. And… he’s from St. Louis :)

In short, he was a transformative hire and badass. He has IT. Well, I’ve NAMED IT. He has ENTREPRENEURIAL RIGOR.

What is Entrepreneurial Rigor and how do I gauge it?

Today I’ll share

  1. What it is and why it matters
  2. My actual interview questions and how I measure it.

Let’s dive in:

My Ampush co-founder and BFF Nick Shah and I coined this term in 2017 when we did an internal culture reboot (reply to this email if you want me to write about that!). What we had observed over helping develop hundreds of people is GOOD people tended to either Hustle meaning they moved fast, were creative, resourceful etc. OR they were rigorous meaning they were logical, quantitative or reflective. But GREAT people were always… BOTH.

To go back to Adam, I first asked him to prototype the entire Kahani “stories” functionality. He pushed back. “How about instead I just build the circles at the top of the screen as a plug in for ecommerce, I can do it in 2 weeks and if no one every clicks on them, what’s the point of doing the rest? If people do click, then I’ll build the rest!.”

Fast, logical, resourceful… you get it.

So we started to break down what we meant by Hustle & Rigor. Then we created this 2x2 to show people where we thought they sat on the matrix and what they needed to do to improve. Then of course, we brought it into our hiring process.


When I was 25 and fresh out of Wall Street, I used to do intense interviews. Gotcha questions, brain teasers and everything in between. Now, for the most part I ask “easy” questions because I’ve learned that someone’s answers reveal a ton about who they are. There was a Google study somewhere that encouraged questions like this. Instead of asking: “how many golf balls fit in a bus?”, ask “Whats the best athletic feat you’ve ever done?” Someone may say “ran a 10 minute mile”, someone else may say “ran a 3 hour marathon.” The question itself isn’t hard but the answer reveals a ton.

For a startup example, “What’s the best marketing campaign you’ve ever run?” They get to choose what’s “BEST” - one person may answer, "I did XYZ that reduced CPA by 50% and grew the brand to millions a month of spend." Someone else may talk about a single ad creative they did. There’s a big difference there.

So here are my questions (short and sweet):

I’d love to hear your story and what intrigued you about this opportunity.

Benign, softball… right? WRONG.

I can usually already tell by this question if I’m excited or not. How? I look for a few things

  • Are they a good storyteller?
  • Does their answer have structure or is it meandering?
  • In their story, do they talk about major decisions and reasons?
  • Do they seem confident, yet humble, and take responsibility?

Then on the second part of the question:

  • Did they actually research this opportunity?
  • Do their reasons for wanting this seem aligned with both their heart and what is right for them?
  • Can they surface parts of their background that make this a strong fit?
  • Are they thoughtful/structured in how they are evaluating this decision?
What’s your 5 and 50 year dream?

What this question tells me:

  • Do we have alignment on the future?
  • Are they ambitious? Do they dream?
  • Can they think at different levels?
  • Are they a risk taker? (i.e. willing to put something out there)

Then my favorite question:

You know this role better than I do, so if you were in my shoes and hiring for it, what do you think are the 3 most important traits we should hire for?

Initially, this tells me if the person is a structured thinker and communicator. And of course, if I agree with their traits. For example, if I’m hiring a CFO and they don’t mention “good with numbers” as one of the traits, the conversation is over.

But let's assume the person nails the 3 traits. HERE is where the question goes next level:

Take a few minutes to think about each trait and come up with your BEST story for when you demonstrated that trait.

A few things I want to see here:

  • Does BEST = results/IMPACT to them? I’m looking for examples where they drove revenue, hiring, something with numbers. Where they moved the needle.
  • Is the story impressive? One time, I had two candidates and I asked for their “best” analytical story. One said: “I made a pivot table” and the other said “I taught myself R so I could analyze 100s of survey results.” What a difference.
  • Is the story relevant? Do they connect it well?

But then, for each story (and I tell the candidate this), I DIG IN 5-10 levels deeper.

Who worked with you on that project? What was the biggest blocker you had to overcome? Were there difficult people you had to deal with? Tell me about how you designed the spreadsheet (or code). What was the best idea you came up with?

Then I go full Entrepreneurial Rigor.

What was the most resourceful thing you did? How did you use numbers to make a decision? How long did that take you? What was the most creative idea you had? What was a time when you reviewed things and changed directions?

What I’m looking for here:

  • Well first, a bunch of the questions are obvious. Note the format, I want them to curve themselves. When they share something resourceful: is it ACTUALLY resourceful? Especially in comparison to others.
  • Depth/Substance. As you can imagine, especially with executives, this is where most interviews go sideways. They nail the story, the traits etc and then I start asking about actual work and they say “oh I can’t remember, not sure about this” or it's just clear they didn’t do the work.
  • I want to hear specifics and I believe whenever someone has deeply owned the project or done the work, they will recall specifics.

The above 5 questions take up the lion's share of the interview, but the next 2 questions help me understand the way they think about working with me.

If this is the best job you ever had in 2 years, what went right?
  • Are we aligned, do they want this for the right reasons?
  • Do they have a clear criteria in their mind for success?
  • Can we deliver what they’re looking for?
Last: What questions do you have for me?
  • Have they been thoughtful about the opportunity?
  • Do they ask good questions?
  • Have they done their homework?

When it's all done, I use a very simple ranking and feedback system:

  1. Strong No
  2. Soft No, but I could be convinced
  3. Soft Yes, but I’m not going to pound the table
  4. Strong YES

I’ll send this around and use it to determine if and who they speak with next.

I also add qualitative feedback, like:

  • Why did they get the rating I gave them (and not 0)?
  • What would make them a 4/4, a strong YES?
  • What areas would I test further?

Learning to hire well is the single most important skill you can develop as an entrepreneur. If you're watching me grow multiple companies at GatewayX and wonder "how does he do it?" understand that's not ME doing. It's the people I hired using this method.

Put tons of time, attention and iteration into building this personal skill and you will make your journey a lot more fun and effective!

Happy Sunday!!

Jesse

Bootstrapped Giants

Jesse Pujji

Bootstrapped to an 8 figure exit @ampush. Now building a $1B+ bootstrapped venture studio @GatewayX and sharing everything I learn along the way.

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