I recently went one-on-one with Alex Levin, co-founder and CEO of Regal.
Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks, or challenges have been most instrumental to your growth?
Alex: In school, I studied philosophy and psychology and realized I did not want to be an academic. I became interested in how technology would impact businesses and started working for startups. Importantly, I’ve worked for a number of startups that didn’t work out, which allowed me to see how different founders built their companies—what worked, what didn’t—and I was able to take the pieces that I liked the most. This was very important. Even in my experience at the last company in the home services space, I was responsible for starting new businesses. I think I’ve started more businesses from zero to a million dollars in revenue than anyone I know, probably more than a dozen. This experience gave me a lack of fear to get started and a lot of knowledge about how to build from nothing, which is very different from working at a big company. This included everything from launching new services, like handymen or electricians, to businesses with retailers selling our services, to launching new geographies all over the world.
Adam: How did you come up with your business idea and know it was worth pursuing? What advice do you have for others on how to come up with and test business ideas?
Alex: The best possible business is one where you’re both contrarian and right. In this case, we have what we call an earned secret. Angi, where I previously led the growth team, lived this experience where we started offering customer self-serve in digital channels, but that wasn’t enough; they still wanted voice. At the time, everyone was saying voice was dying, but we saw that customers deeply wanted it. We knew we were right because of the experience we’d had, which gave us a leg up over everyone else because we were both contrarian and right. A lot of the people who told us we were completely wrong in the early days now have come back and tried to invest in us, which is a good feeling.
Adam: What are the key steps you have taken to grow your business? What advice do you have for others on how to take their businesses to the next level?
Alex: The number one thing I would leave you with is that, as a marketer, you’re taught that you have to reach a customer five, six, or seven times before they buy your product. This is why everyone does cross-channel marketing. It might involve seeing a story in the paper, a display ad on a website, a poster outside of your building, a digital ad, and then finally, when you’re looking for something, ChatGPT tells you about a product, and you recognize it as the default product. As a founder, it doesn’t feel that way at the beginning. You feel like if you tell somebody something and they don’t immediately buy it, everything is over. You have to remember that you need to reach people multiple times before they’re going to buy your product.
One consequence of this is that it’s more important to deeply target a few people on many different channels than to spread your efforts too widely. However, many founders have products that are nice-to-haves. As a founder, you may have seven slides of the things you’re going to build, but you’re lucky if people are reaching across the table and saying, “I need that thing now. How do I get it? I’ll pay anything for it.” If you don’t have at least one thing like that, you don’t have a business. Don’t feel like you have to build everything; find that thing that people need now.
Adam: What are your best sales and marketing tips?
Alex: My best tip is to pick up the phone. Something I see constantly, especially with newer reps, is that they’ll have a great discovery call, demo, and executive conversation, and then the moment things get tricky, like questions on pricing or contract terms, they retreat to email.
That’s almost always a mistake. I watched a rep nearly lose a $120K deal doing this. Negotiating over email means you can’t hear hesitation, you can’t tell why someone’s really asking what they’re asking, and the whole thing turns into a numbers fight instead of a conversation about the relationship you’ve built.
Adam: What are the most important trends in technology that leaders should be aware of and understand? What should they understand about them?
Alex: I don’t think it’s a secret that AI is changing every business. First, it was changing how people code, transitioning from building everything themselves to working with an agent on their behalf. Now, this is happening in marketing teams, sales teams, and people teams. It’s changing the expectation of how you do your job and how many people are needed at companies. Correlatively, companies of the future will have fewer people and more vendors. They will have lower communication tax, and each person will do many more things and have to switch contexts more frequently.
Another major shift is the speed of execution, which is accelerating drastically. It used to be enough to have built a nice software product because that was hard. Now, if someone sees a nice software product, they can ask a coding agent to make it instantly, so they’re quick to copy that. This means you have to build towards advantages in underlying technologies that can’t be seen, or in distribution, integrations, or go-to-market strategies, which will continue to be sustainable because they can’t just be copied by an AI agent.
Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?
Alex: The hardest part of being a founder, or any leader, is knowing when to stick to your vision and when to take contrary feedback. Sometimes, you can have a long-term vision that’s very clear, like Elon Musk’s vision of going to the moon, but in the short term, you have to make many different decisions and changes to get there. As a founder, sometimes your long-term vision needs to be challenged and changed a bit before it’s fully proven ready.
Adam: What is your best advice on building, leading, and managing teams?
Alex: Old companies used to have a thousand employees and ten vendors. In the future, companies will have ten employees and a thousand vendors. Strong AI will allow you to move faster, have less communication tax, and enable each person to do more. It’s a complete rethink of what it is to be a manager; it’s not just managing humans, but also managing AI and technology to maximize efficiency and speed.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Alex:
1. Don’t be scared to do something just because it’s risky. I tell every aspiring founder to work for another company first, take big swings there, and learn from failures on someone else’s dime.
2. Be willing to walk away from a deal that isn’t a real, mutual partnership. Even if an opportunity looks great on paper, shifting terms, unreasonable asks, or lack of collaboration are red flags. I once walked away from a $200K ARR deal because of this, and it was a reminder that strong partnerships matter more than revenue alone.
3. It’s not always the best move to chase whatever’s getting hype. Look to the industries everyone else is ignoring and think about where you can actually create value.
Adam: What is the single best piece of advice you have ever received?
Alex: You should be willing to do things that don’t scale. This is a famous piece of advice from Y Combinator. Fly in person to meet people, interview every customer you have for the first 100 customers, and manually onboard people before anything else is possible.
