I recently went one-on-one with Michael Wolf, CEO of ResortPass.
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 have been most instrumental to your growth?
Michael: I never thought I would end up in business. My undergrad major was history, and I thought I would end up doing something in government. Every summer was spent in DC trying to build a resume in that direction and build the right connections.
That changed when Bain came to campus to recruit consultants. I hadn’t considered Bain as an opportunity, but everyone I met was really impressive and engaging, and I wanted the opportunity to learn from them. I gave consulting a chance, and those ended up being three of the most formative years of my career.
Bain was my first exposure to the business world, and it taught me that I enjoy being an operator in fast-moving settings. There were 14 people in my Bain class. 13 went into private equity, and I was the only person who chose to go into startups. This was 2005, so the number of true startups was limited in New York – it wasn’t anything like today. I literally made a list of the 30 companies that fit my goals and started reaching out.
My first landing was at a startup that was ahead of its time. I joined a company that was a pioneer in targeted ads for television. The idea was strong, but the market wasn’t ready, and the infrastructure wasn’t there. It was a hard lesson in how much timing matters, and how even the best ideas have to coincide with the right conditions to really take off.
Since then, I’ve spent the last 20 years helping build startups, mostly focused on consumer marketplaces.
Adam: In your experience, what are the key steps to growing and scaling your business?
Michael: It’s cliché, but it’s true. It’s all about the team. There’s nothing more important than having the right people around you. I think one of the biggest mistakes people make is rushing that process. You really need to spend a disproportionate amount of your time on it, and make sure you hire the right people.
Adam: What are your best tips on the topics of marketing and branding?
Michael: It’s easy to get caught up in tactics, channels, and what’s working at the moment. But those are just means to an end. The best brands are very clear on what the moment is they’re building toward.
To me, there is no better example of this than my time working on the Obama campaign. In 2007, I walked into the 500-square-foot HQ for Obama’s campaign on Fulton Street, introduced myself, and asked how I could get involved at a senior level. The guy handed me a sign that said “Obama” and told me to go stand on Wall Street and hold it up. That was the first thing I ever did for the campaign.
Every conversation, every event, every door I knocked on, all laddered up to one moment: election night at 11:00 pm Eastern on CNN when the winner was called. It didn’t matter what had happened along the way if the outcome wasn’t reached.
That experience shaped how I think about marketing. Everything should be in service of a moment that matters. The question isn’t just what tactics you’re using, it’s what you’re building toward, and how you create something people remember and want to be part of.
Adam: What do you believe are the defining qualities of an effective leader?
Michael: Your role as a leader is to inspire your team, your customers, and your partners. It’s imperative that your excitement is genuine. Ultimately, you have to be the biggest advocate for what you’re building in the world. If you don’t actually feel that, people will know.
The other piece is being unapologetic about who you are. Your leadership style, what you expect from people, and how you show up. There’s something really powerful about being direct. It can feel uncomfortable, but it makes you more effective. People know where they stand, and that builds respect over time. You see this in leaders who are very clear about expectations and accountability. They’re direct, but they’re trusted because of it.
Adam: How can leaders and aspiring leaders take their leadership skills to the next level?
Michael: My best advice is to surround yourself with others who have the same job. There’s no one better to learn from than someone who is going through it at the same time as you. The most cathartic moment of my week is having dinner with other CEOs. Sometimes, that’s an organized group dinner, and other times it’s 1:1. But there is always something I learn from hearing what is happening at other companies and how different people are navigating those challenges. You learn a lot, both the functional stuff like how someone runs their all-hands or manages their org, and the very specific, one-off challenges that only someone in the exact same position can really understand. The most practical, most relevant lessons I’ve learned have come from my peer set, not from a book or a course.
If you are newer to an industry or first stepping into a leadership role, I think you will be surprised by how responsive other founders and CEOs are if you just reach out to them. I love when people reach out to me. Having been on the other side of it, I’m empathetic to the journey. You have to invest time in building those relationships. The startup world, more than most, is very open to it, and you should put the work in to make sure you have connections with other leaders in your industry.
Adam: What are your three best tips applicable to entrepreneurs, executives, and civic leaders?
Michael: First, make sure the business you’re building is something you genuinely love. There are going to be a lot of hard days and a lot of great days. Caring deeply about what you’re building will be the thing that keeps you moving forward.
Second, don’t underestimate how much you can differentiate yourself through responsiveness. Following up, getting back to people quickly, doing what you say you’re going to do. It sounds simple, but it really stands out.
Third, know what you need to be effective. For some people, that’s coffee, for others it’s working out, meditating, or something else entirely. It’s not one size fits all, but you have to be intentional about the routines and habits that allow you to show up at your best.
Adam: What is your best advice on building, leading, and managing teams?
Michael: Again, it all comes down to hiring the right people. I call it hiring for World’s Best Talent, which means hiring people who are incredibly good at what they do and considered some of the best in their field, but who are also, at their core, good people. People get their energy from people, and you want to make sure your team is filled with people you can’t wait to collaborate with and who motivate you. That energy compounds. It shows up in how teams work together, how they show up for customers, and how the company grows.
Once you have the right people, you can lead through inspiration. You can create an environment where people feel like they’re part of something meaningful and want to bring their best every day. But it starts with being patient in the hiring process.
Adam: What is the single best piece of advice you have ever received?
Michael: Most decisions don’t matter. It sounds counterintuitive, but it’s freeing. You can spend a lot of time overanalyzing things that ultimately won’t have a meaningful impact. The key is to move quickly, make the call, and keep going. Save your time and energy for the decisions that actually matter.
