I recently went one on one with Michael Segal. Michael is founder and CEO of Skylight, a maker of connected devices for the home that hundreds of thousands of people use to bring their families closer together. Previously Michael was Vice President at Bessemer Venture Partners, a venture capital firm where he championed investments such as Guild Education (which helps large company employees get their college degrees), Groups (which helps people with opioid addiction get affordable treatment), and Periscope Data (which is helping usher in the data-driven enterprise).

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? 

Michael: I studied biochemistry in school, and then immediately got into tech startups upon graduating – first as a junior VC investor at Bessemer, then as an entrepreneur. VC taught me what successful startups looked like, and how successful entrepreneurs and investors analyzed businesses and opportunities. It did not teach me how to actually build a team or product to success, and my first startup adventure was a failure. It also turned out to be the best education of my life. You don’t know what you’re capable of, or what your strengths and weaknesses are, until you try something really tough and fail. It hurt, but it was pivotal for my development as an entrepreneur and leader.

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?

Michael: Some friends and I were brainstorming what the ideal gift could be for a parent and grandparent. We were thinking about a service that printed photos each month and sent them by snail mail – what parent or grandparent doesn’t love photos (or hearing from their kids)? I said “Why not just have a device that you can send photos to, and they pop up in mom’s home?” The rest is history – we’ve sold hundreds of thousands of Skylight Frames since then. I would say the reason this idea turned out to have such legs was because it was a sincere and genuine need for me and my family. That personal need is always the best compass for any business, but particularly a consumer business. And it’s deceptively hard to get: as soon as you’re building something for someone who is not you, the problem of understanding their psyche and creating something incredible becomes 10x harder.

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

Michael: First, we just asked people. For a meaningful portion of them, their eyes lit up when they heard the idea, and they were clearly excited to buy. This also helped arm me against the frequent feedback (e.g. from investors): “Doesn’t this already exist?” My answer to myself was simple: maybe it does, but if all of these people are surprised and delighted by the concept, then the market has not been won yet. We then launched a test website, and made a first batch of 40 units, and the orders flew off the shelves in a couple days. I knew from previous ventures how hard it was to get anyone to buy anything, so this was an extremely positive signal, at a small scale. But even then, it took 3 more years before we figured out a business model that allowed us to build a big business. So I guess the takeaway is: talk to potential customers, build stuff that genuinely excites them (and not just because they’re being polite). And finally, if you have lucked into making something people absolutely love, even at a small scale, hang on tight and keep going.

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? 

Michael: The key for us was finding a winning marketing approach. To get there, we needed to reinvent our product to support a higher price point (and therefore more margin for marketing). We then had to figure out the times of year, and the messaging, that allowed us to market profitably. All of this sounds easy in retrospect, but there were many months of stasis and uncertainty, and lots of dead ends. The key was to keep going, keep trying stuff, until we found something that worked. To have this kind of patience, you have to have intense conviction that you’re building something the world wants and needs, so that’s always step #1 (as aforementioned).

Adam: What are your best sales and marketing tips? 

Michael: On a micro level, you need to grab people’s attention, and get them excited in the 5 seconds you have before their attention runs out. That’s true in the offline world, and it’s certainly true in social media advertising. From there, you just talk to them like a real human being: here’s what we offer, here’s why people love it, here’s why you should feel comfortable buying it. And then you take that show on the road, to every marketing channel you think is worth trying, until you find something that scales!

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? 

Michael: I value self-awareness, empathy, a strategic mind, and a bias for action. All of these are things most of us believe we have, but in practice they’re not so easy. It’s hard to be self-aware when that means facing down your most shameful weaknesses. It’s hard to be empathetic when the stakes are high and you are feeling scared and frustrated. It’s hard to be strategic when you are constantly bombarded by small stuff that fills your day. It’s hard to have a bias for action when the right answer is almost always unclear. But the point is, these are all muscles that we can work to strengthen. Our tools for that are reflection, external feedback, optimism, and a passion for self-improvement.

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

Michael: Hire people who impress you with their intelligence and energy and potential (and ask them to do a project, because interviews are a terrible way to judge people). Genuinely care about the people you hire – their career, their work satisfaction, their learning and growth. If you give them work that challenges them and helps them become the person they want to be, they’ll do great work for the company. When they don’t ace something, instead of jumping in and taking the reins, realign on expectations and empower them to try again. Keep standards high, but instead of blaming or chastising, coach them to be the star performer you know they can be. 

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

Michael: “It is only with the heart that one can see rightly; what is essential is invisible to the eye.” - Antoine de Saint-Exupery, The Little Prince


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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