SG x Deon Nicholas: on Forethought's acquisition and Espa's launch

Image Credit: Espa

The Forethought acquisition was the headline. The more interesting story is what came after it, and what had to happen before it. In a conversation with SG CEO Lesley Gold, Deon Nicholas talks about building and selling Forethought to Zendesk, launching Espa — an AI executive assistant that just launched with the support of SG— and why the hardest thing he had to learn wasn't about business at all.

SG: You're part of a very small club of founders who've had a successful exit and decided to do it again. When you're starting a company, what are the decisions that actually matter from day one?

Deon Nicholas: It boils down to three things. Product-market fit: obsessing over what problem you're solving, getting something into real users' hands as fast as possible, and doing cycles and cycles of testing and iteration. That's where 90% of companies fail. Team: finding the core people who round out your superpowers and fill the gaps you're not willing to admit you have. And distribution: how do you actually get your product into the hands of users? If you do those three things well over a compounding period of time, you'll get the critical velocity you need. The rest is grit.

SG: You've talked about storytelling as a superpower you almost didn't claim. What was holding you back, and how did you work through it?

DN: I grew up in inner-city Toronto. Humility was core to who I was. The idea of building a big personal brand felt vain. I could literally hear my mom's Caribbean accent, her voice of disappointment. My executive coach pushed me to actually have those conversations with the people I was most afraid of letting down. I called my mom. She wasn't disappointed. She was proud. And something shifted. A lot of that early coaching, what my coach called context coaching, the emotional infrastructure of leadership, was really about coming into my own as a leader in a world I didn't grow up in. I had serious imposter syndrome. I knew how to chase a problem and solve it, but the idea of being larger than myself felt, I don't know, icky. Working through that, realizing it would actually be better for the company, better for the people I was trying to reach, that's when I started leaning into it. In hindsight, storytelling and brand-building are probably my biggest superpowers. But in 2018, there's no universe I would have said that.

SG: LL Cool J and Gwyneth Paltrow are both Forethought investors. That doesn't just happen. How did it?

DN: It's about humans. I posted on a forum for NEA-backed CEOs asking for advice on how to tell our story better. Three CEOs responded. One of them was Gwyneth Paltrow. I went through a few stages of denial... oh wow, that's the same name as the actress, probably her assistant, wait, maybe it's actually her. We got on a Zoom call mid-COVID. My son was running around. Her son had just gotten back from skateboard camp. We were just two people trying to build something. She's one of the most generous humans I've ever met. She saw a fellow founder and just wanted to help. LL Cool J gave me the line I still carry: have the confidence to be humble. Know your strengths, know your weaknesses, and understand that the two can be truly combined. The broader lesson is: have a story worth telling, and lead with what value you can bring, not what you need. Give energy first. That's it.

SG: You're unusually good at blending the personal and the professional, especially on LinkedIn, in the press, and in how you talk about your companies. How do you do it, and how can people who aren't you do it?

DN: Lead with authenticity, but I think it goes a layer deeper than that. Every story worth telling starts from curiosity or emotion — something that's actually happening in your life. So whenever I post something or go to the press with something, it always starts there. What am I actually feeling? What is actually true for me right now? There's a self-awareness required for that — the ability to almost observe yourself. To zoom out, notice what you're experiencing, and ask whether there's something worth sharing in it. I think a lot of people skip that step and go straight to what they think they should be saying. The ones who connect are the ones who start from something real.

SG: Tell us the Espa Labs story. Why does the world need it, and what does it actually do?

DN: When I was scaling Forethought, I had an executive assistant. That support made an enormous difference — keeping everything together across work, family, all of it. Most people don't have access to that. A freelance designer, a realtor, someone trying to build something without VC backing — they're all carrying the same weight without any of the infrastructure. Espa is the AI executive assistant for everyone. It goes wherever you go and actually executes: sends the email, books the meeting, and tracks the follow-up. My wife and I are already using it to manage our family's schedule. The whole idea is that executive-level support shouldn't be a perk. Everyone deserves that kind of help. That's what we're building.