I recently sat down with Jeff Hirsch, Founder & CEO of Executive Guru and a leader with decades of experience in tech, media, and advertising. He’s led multiple businesses to successful exits, and now he advises startups on growth strategies, leadership, and navigating the challenges of scaling.
This week, Jeff talks about what it takes to lead a startup effectively—balancing the emotional investment founders have in their businesses with the practical decisions needed to grow. We broke down everything from building leadership teams that can scale with the company, to making tough calls when you don’t have all the data, and getting the most out of your board.
If you're struggling to balance your passion with the demands of growing a company, Jeff has practical ideas to help you find that sweet spot.
Below are some highlights from our conversation — but to get the most out of Jeff’s expertise, I’d watch the full episode here: howtounfuckyourstartup.com
Jeff Hirsch: I started in sales and advertising while still in college, selling ads for the school newspaper. That’s when I realized I enjoyed solving people’s marketing problems. After college, I had a short stint in radio and eventually started my own advertising agency on the central coast of California. It grew to 25 people and hundreds of millions of dollars in billing—all built on our credit cards.
From there, I started a software company with a friend, selling systems to film and video production companies. That business made the Inc. 500 list. Eventually, I moved into ad tech, founding a company called ValueClick. We saw the potential of bringing offline media models into online advertising. Later, I co-founded FastClick, which went public shortly after its Series A. Most recently, I was with Pubmatic, where we went public during the pandemic, and now I run a consulting firm called Executive Guru, helping founders and companies grow strategically.
Jeff Hirsch: It’s a tough choice whether to raise money or not. If you can avoid raising funds, that’s great, but sometimes bootstrapping can put you at a disadvantage against competitors who have more resources. Founders often don’t realize how costly giving away equity can be down the road. Dilution can hurt your ability to raise more money later. If you raise money, make sure you structure the deal properly. You need a trusted advisor to help navigate these decisions, so you don’t end up in a bad situation where you’re left with little negotiating power.
Jeff Hirsch: I look for humility. It’s a key leadership quality, especially when taking feedback. If a founder can’t take input from investors or their team, it’s a bad sign. They won’t be able to grow as a leader, and that will hurt the company in the long run. I also pay attention to whether the founder can balance data-driven decisions with intuition. Data is crucial, but sometimes you don’t have all the data you want.
Jeff Hirsch: I follow Colin Powell’s rule—he talks about making decisions with 40-70% of the information. If you have less than 40%, you don’t have enough to act. If you wait for more than 70%, you’ve waited too long, and the opportunity is probably gone. Experience helps fill in the gaps when data is missing. It’s all about pattern recognition. The more you’ve seen, the better your intuition becomes, and that helps guide decision-making. That’s why it’s also so important to have diverse perspectives on your board—different experiences create different patterns, and that leads to better decisions.
Jeff Hirsch: When I first became a CEO, I thought board meetings would be these dynamic discussions where we’d solve all the company’s problems. But board meetings are really more about getting approvals and addressing specific points. What I found helpful was meeting with board members individually before the actual meeting. I’d go over everything I wanted to discuss, so by the time we got to the board meeting, they were aligned with the issues at hand. That allowed for more dynamic conversations and better decision-making. Founders should take that one-on-one time to really dig into the issues and get the most value from their board.
Jeff Hirsch: The key is to think from the board’s perspective. Don’t fill the deck with what you think they want to see—figure out what the board really cares about. They want a true picture of the company’s state, not just a "look at our numbers" presentation. Be prepared for real conversations, and focus on the areas where the board can provide valuable insight. Also, once you bring something up in a meeting—like your sales closing ratio—plan on talking about it again. If you highlight an issue, the board will expect updates at every meeting going forward, so make sure it's something worth discussing long-term.
Jeff Hirsch: I always tell people I promise two things: recognition and respect. No matter what, those are in my control. I don’t take credit for other people’s work, and I always make sure to acknowledge what others have done. Values need to be lived by leadership; otherwise, it destroys morale. People need to feel proud of the culture they’re part of, and that only happens when leaders are authentic about their values and actions.
Jeff Hirsch: One of the most important things I learned is the value of over-communicating. I assumed smart people would just figure things out, but I learned that being explicit about direction and expectations produces much better results. I also used to send a "Monday Missive" email to the whole company every week. I’d include a few things that were going on, so everyone always felt in the loop. It’s easy to assume that because you’re living and breathing the company, everyone else knows what’s going on. But they don’t, and you need to make sure they do.
Jeff Hirsch: One of the most common leadership issues I’ve seen is founders refusing to adapt. They’ll stick to the mindset of "this is how we’ve always done it," even as markets and customers evolve. This resistance to change, despite input from smart people they've hired, becomes a major barrier to growth. Passion is important, but it can cloud judgment when founders believe their way is the only way—until it no longer works. Those who can self-reflect, embrace new ideas, and adapt are the ones who succeed in taking their businesses to the next level.
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