My message to Daksh Gupta

Last week I wrote that Daksh Gupta (CEO of AI startup, Greptile) was right about needing to go all-in.

Most faith-driven entrepreneurs ARE too comfortable. We domesticate our walk with Jesus, making it fit in nice little boxes we can manage. We DO need more intensity.

But then he said this: "As we mature we'll hire older, more experienced people who have families and can't work 100 hours a week."

Gupta, brother, as a 41-year old dude, married, with 3 kids, and who’s also in the startup game let me share some perspective:

You're right, I can't work 100 hours a week. Haven't been able to since 2014 when Julian was born.

But here's what I did do: After our exit, with money in the bank and security achieved, we went all-in on our next venture. Sold everything—401k, cryptocurrency, everything but the house.

I did it in agreement with my wife. Something we discerned, talked about, prayed through together.

Could've coasted. Instead, she agreed to start over at the bottom. Startup grind. Back to fundraising. Back to uncertainty.

That agreement gave me permission to build differently.

A friend and former mentor of mine, Kevin Penry, frequently challenged me to not view the world through a binary lens. Hours in = results out. But it's not that simple.

When Grace green-lit this journey, she didn't just approve a career pivot. She was saying: "Even with three kids and a mortgage, I've got your back. We'll scale down. We'll focus on what matters. In all the uncertainty, all the sacrifice, all the moments where it feels like it might not pay off—I'm here."

That kind of support doesn't divide your capacity. It multiplies it.

Here's what else hours don't measure: character.

Skill is par for the course. But I care more about character and team compatibility than a pure output calc. People of good character who align with the mission will naturally work hard. You won't need to convince them.

Without character vetting, you get people working late for optics. Employees who can't push back because they're afraid. Marriages crumbling because someone followed your vision too devoutly to speak up about being overworked.

The last thing I want is someone's family destroyed because I created a culture where speaking up about boundaries equals weakness.

But I guess you don't need to worry about that since you're not currently hiring people with families.

Look, I understand the need to filter for commitment. I agree with that goal. But despite his age and success, his comment reveals something deeper in the heart and values.

So where does this leave us as faith-driven entrepreneurs?

Go all-in on your venture. Sprint when it's time to sprint. Rest when it's time to rest.

If you're married with family, that's your unfair advantage—not your limitation. Your spouse's belief in the mission changes everything. Don't let the entrepreneurial patterns of the world tell you otherwise.

If you're single, embrace the freedom and capacity that brings. That's also a gift. Pray for people who'll keep you accountable and encourage your journey.

Either way, remember: Jesus is after your heart, not your hours. When hearts align with mission, intensity follows naturally.

I’ll end with a verse:

p.s. I’m aware the context of these quotes came in 2024. Things could have changed. From time to time I’ll be reminded of what Gupta had said and how he was hiring. If he ever reads this I want him to be encouraged around the all-in attitude for a tech startup, especially one such as Greptile. I also wanted his heart to be challenged around the idea of families.