What qualities do you look for when evaluating candidates?

I look for people who are comfortable taking initiative. They don’t wait around for instructions – they see a problem, work toward a solution, and take ownership of the outcome.

In many ways, the best employees are a little entrepreneurial themselves. You can usually spot that during the interview process through the questions you ask and how they approach real-world solutions.

What lessons from building Proper have you applied to Wister?

People often say your first $1 million is the hardest to make, and I think there’s a lot of truth to that. Every time you do something, it gets a little bit easier, and you learn from the past.

Building Proper gave us the confidence to move faster with Wister. We have a better understanding of the market, know where to focus our energy, and as a result are putting key people in leadership roles earlier than we did the first time around.

What gave you confidence that Wister could become a scalable business?

The key is to figure out your close ratio. Can you consistently sell the product? When the answer is yes, that is the tipping point. Every entrepreneur has an idea, but until you test it in the market, you don’t necessarily know how consumers are going to respond.

You also need to understand the size of the opportunity. A great product doesn’t mean much if the market is too small. With Wister, we had confidence in both the demand and market size. We knew there was a real need and that customers were willing to buy what we were offering.

Once you reach that point, the challenge shifts from proving the concept to scaling it. It becomes about the mechanics of advertising, marketing, and lead generation.

What kind of culture have you worked to build at Wister, and why is it important to you?

Our culture is built around a simple philosophy: “If you're not happy, I'm not happy.”

That’s a big responsibility as a leader, but I believe that when your employees are doing well – personally and professionally – the company benefits as well.

When our founding fathers started this country 250 years ago, they wrote “life, liberty, and the pursuit of happiness.” I’ve always been struck by that phrase. They understood that happiness is not a guarantee, but what matters is having the opportunity to pursue it. Because work is such a big part of our lives, I think business owners have a responsibility to create an environment where people can succeed and find fulfillment. That mindset influences how I approach leadership. One of the most rewarding parts is helping people reach their potential.

Picture your employees driving to work each morning. If they are dreading the day ahead, you are not going to have a successful business. But if you can find a way for someone to get into their car and think, “I’m looking forward to walking through that door today,” then you have an absolute home run. That’s the kind of culture we’re striving for at Wister.

How do you preserve culture as a company grows?

You duplicate yourself – find people who buy into what you're building, and then empower them to lead. As a company grows, you can’t personally touch every decision. Culture has to be delegated and reinforced through strong managers who understand the organization’s values and model them daily. That’s why getting your management team right is so important. With the right leaders in place, the culture can scale right alongside the business.

As someone whose business revolves around managing risk, how do you think about risk-taking as an entrepreneur?

The classic line is that the higher the risk, the higher the reward. There’s certainly some truth to that, but I don’t think entrepreneurs should take risks blindly.

Before committing your time, money, and energy to an idea, get it down on paper. Write a business plan, run the numbers, look at a pro forma, and test drive the concept. The more homework you do upfront, the better you understand the risks you’re taking.

There’s always an element of risk in entrepreneurship, but one of the best pieces of advice I learned from a business partner years ago was: If you bet on yourself more times than not, you’re going to win.

How do you see the short-term rental industry evolving over the next few years, and what opportunities do you see ahead?

The short-term rental market has been shaped by regulation over the past decade. Some communities have embraced it, while others have tried to limit it, often by restricting supply. As a result, growth has been relatively flat in many areas over the last five years or so.

Long term, though, I think that pendulum shifts back. People continue to place a greater value on experiences and time with family and friends. Vacation rentals fit directly into that, which makes this an exciting industry to be part of.

Regulation will continue to be an important factor. Short-term rentals are often blamed for housing affordability challenges or neighborhood concerns, but the reality is usually more nuanced. That doesn’t mean there shouldn’t be rules – reasonable oversight, safety requirements, permits, and fees all have a place – but an outright ban is different.

Ultimately, I think we’ll continue to see states and municipalities move toward more balanced approaches rather than blanket restrictions. Property owners should have some ability to determine how their property is used, and in the long run, I think common sense will prevail. That’s why I’m optimistic about the future of the industry.

What’s one piece of advice you wish someone had given you when you were first starting to build your business?

One thing I wish I had understood earlier is that building a successful business requires being all in. It becomes your everything in a way you don’t fully understand until you’re in it. When we were building Proper, I devoted everything I had to making it succeed.

What I didn’t appreciate at the time was how easy it is to let everything else take a backseat. When you’re building a business, there are always demands on your time, more opportunities to chase, and more reasons to keep pushing.

It is important to be intentional about making time for the things that help you perform your best, whether that’s your health, your family, or simply creating space to recharge.

If I could give one piece of advice to entrepreneurs, it would be this: Bet on yourself, and go all in – but don’t do it at the expense of yourself.

Darren, thank you for your time and insights.