I recently went one on one with Jay Bregman, the co-founder and of Thimble. Prior to Thimble, Jay founded Hailo, a ridesharing company in London backed by investors including Sir Richard Branson that was acquired by Daimler. Earlier, he founded and sold eCourier, a technology-enabled services company to Royal Mail, the U.K. equivalent of USPS.

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? 

Jay: I’ve been in the startup world for quite some time now. My father invented a heart device, which really led my family to be super supportive of my pursuit of invention. The first startup I founded was called eCourier. It was a technology-enabled services company which I sold to the Royal Mail, the U.K. equivalent of USPS. Then I founded a London-based ridesharing company called Hailo which was acquired by Daimler in 2016. 

eCourier was growing quickly when the 2008 recession hit, which was really unfortunate timing because it felt like business fell off a cliff virtually overnight. Looking back now, that time was one of the best educational moments that helped prepare me for future stress because it taught me that an essential quality of entrepreneurship is learning to roll with the punches. In many ways, it made my following ventures even stronger and prepared me as a strategic business leader throughout our current pandemic.

Now I am back in NYC working on my third venture -- insurtech startup Thimble, where we help small businesses succeed on their own terms. My prior experience in startup work and leading in times of crisis have prepared me well to manage and grow Thimble during this time and meaningfully help the small businesses we cater to.

Adam: How did you come up with your business idea? What advice do you have for others on how to come up with great ideas? 

Jay: To me, getting involved in markets when there’s so much room for innovation and growth is the key, and that’s one of the reasons why I love insurance and what we’re doing at Thimble now. Our main goal is to make insurance simple so small businesses can succeed on their own terms. The need for this simplicity and flexibility is important, now more than ever.

Adam: How did you know your business idea was worth pursuing? What advice do you have on how to best test a business idea? 

Jay: During my time building Hailo, the whole idea of using a smartphone to secure more work was fascinating to me and is a concept I always thought about. More importantly, however, I saw a gap in the market. By 2027, the majority of the U.S. workforce will work as freelancers or contract workers. For people engaging in this type of work, many clients require them to be insured. These workers need convenient access to quick, flexible insurance policies so they never lose a potential job or have to call an insurance broker -- a stark contrast to the binding, annual policies that are typically available. 

In order to best test a business idea, you must consider if what you’re building is something that can last. I’ve seen businesses that have been sold very quickly because they were originally built to do just that. But that should not be the goal for launching a business. It is also very important to surround yourself with a competent team that is equally as passionate about the mission of the businesses and is willing to put in the needed time and effort to test, revise, and grow the idea. 

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? 

Jay: My prior startup experience definitely helped me take Thimble to the next level and scale the business on a rather fast timeline. I made sure to acknowledge the mistakes I made in the past as I started Thimble. That’s definitely a huge aspect of entrepreneurship - more than likely, an entrepreneur isn’t going to land his or her big idea on the first try. So as we move forward in our careers, we have to keep the lessons we learn top of mind to prevent repeating history. 

My advice on how to take a business to the next level is to understand at a really foundational level the needs of the people you’re catering to. For example, when we started Thimble, it was imperative for us to speak face-to-face with real business owners to obtain a truly sincere and authentic understanding of their insurance needs. Through these conversations, we realized that people were frustrated with the complicated annual insurance policies that were often very difficult to navigate, so our first step was to find a practical solution. When you develop an understanding of these needs, your next business steps become much clearer. 

Adam: What are your best sales and marketing tips? 

Jay: For marketing tips, I think it’s important to not undervalue how important the name is. The name of your company often determines the trajectory of your branding and messaging, and successful companies do a great job of cohesively linking the name to key aspects of the company. For example, Thimble -- initially called Verifly -- represents protection for businesses/creators, just like our company. 

It’s also very important to clearly communicate your company’s mission statement to your customers, your investors and your employees. It reminds everyone what the purpose of the company is in a really concise and easily digestible way. Our mission statement at Thimble is to make insurance simple, to help businesses succeed on their own terms. We refer back to it constantly to remind ourselves and others what the ultimate goal is at the end of the day.

For sales tips, simply, businesses should know who their target is and learn the best ways to effectively reach those people. It goes back to understanding the most basic needs of your consumers and moving forward from there. I also think it’s important, at least in insurance and related fields, for your product or service to be straight-forward and easy to navigate. Prevent as many barriers to entry as possible and your customers are more willing to engage with your product.

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? 

Jay: I believe that an effective leader, above all else, stays calm. A key takeaway from my experience as a CEO during the 2008 recession was the ability to remain composed when the next stressful situation presented itself. The ability to maintain a state of real relaxation in the face of danger allows you to see opportunities that you would never notice when stressed or on edge. 

It is also imperative that CEOs take care of themselves. Your mental clarity, sense of calm, environment, and sleep habits — all of these basic needs must be given proper attention, especially when business turns bad. Uncertain, stressful times are exactly when the company needs you most, and your clarity will reflect on the entire organization, as well as your investors. 

Adam: What is your best advice on building, leading and managing teams? 

Jay: When I was in the process of building Thimble, I wanted to be with people that I absolutely loved and would enjoy working with in both the good and bad times. The team was fabulous in both the first two businesses I founded, but I think it’s even better with Thimble because I prioritized the consideration of team dynamic, multifaceted skill sets, and made sure the team would be able to function at a high level of calmness and efficiency in times of stress or uncertainty. I’m really proud of the culture our team has built at Thimble.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders? 

Jay: My first tip for any type of business executive or leader would be to know when and how to pivot quickly. We tend to be extremely loyal to projects we’re passionate about, but at a certain point, it’s important to accept if something isn’t working anymore in order to quickly move on to another opportunity. As I mentioned previously, it’s part of our mission to “think wild but act tame.” You can have the biggest, most industry-forward ideas, but in order for those to come to fruition you also need to be practical and realistic to a certain degree. 

I think COVID-19 is a perfect example. The pandemic really threw a wrench in peoples’ plans across the globe and required us to look at the bigger picture, reassess our priorities, and evaluate the best way to move forward and realistically bring meaningful change into the marketplace. I’ve had to learn this hard lesson many times throughout my career, but it’s a really valuable lesson to take with you moving forward, especially in entrepreneurship. 

Second, it is important to remember to take care of yourself as well as the business. You are in a better position to lead the company during every letdown, disruption, and environmental exogenous issue when you are in a healthy headspace and can think clearly to make the best decisions for all stakeholders involved.

Third, as mentioned previously, make sure that whatever you are building, that it is built to last. Many people are making the leap to start their own business in spite of or because of the current climate, but it’s important to be clear on what exactly your value add is in order to ensure longevity for the company. Now more than ever, it is essential to consider factors such as scalability, profitability, independence, and leaving a lasting effect of and for your business. 

Adam: What is the single best piece of advice you have ever received? 

Jay: I think the best piece of advice that has had an invaluable impact on how I operate as a CEO has been to use habits as a guide. I’ve learned that there are key habits that every business leader should adopt, like pacing yourself, staying active, recovering, and embracing routine. 

It seems counterintuitive for a CEO to say the best advice they received is to prioritize self-care, but it's true. The more that I enforce my own recovery by going to bed and waking up at the same time every day, and disconnecting for an hour during lunchtime, the better I perform as a CEO and business leader.

Adam: Is there anything else you would like to share?

Jay: I know that the pandemic has exponentially increased the stresses on business leaders and businesses alike. In times of disaster, there is a huge premium on both capital and clarity. The capital you have available may be beyond your control, based on where your business happens to be in the funding cycle when the world tweaks. But clarity is always in your control. Use it wisely.