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Michael Segal: “People stuff”

The “people stuff” is always the hardest. When people get upset at you (or vice versa), it can be so energy draining. Conflicts will arise, but life is always better with more communication, assumptions of good intent, etc. As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of […]

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The “people stuff” is always the hardest. When people get upset at you (or vice versa), it can be so energy draining. Conflicts will arise, but life is always better with more communication, assumptions of good intent, etc.


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Michael Segal.

Michael Segal is founder & CEO of Skylight (www.skylightframe.com). Skylight makes 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 funding 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).

Michael received a BA in Biochemistry from Harvard College in 2008, and an MBA from Harvard Business School in 2015.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

I was a biology major in college, without a glimmer of entrepreneurial experience. But I always knew I wanted to make a significant impact, bring together an awesome team, and most importantly bring something totally new into the world. It was that last notion that really sang to me: building something new sounded like a romantic adventure, and that’s what I felt I wanted in my career. Maybe it wasn’t the traditional path, or the one I was “supposed” to be in (what about that MD or PhD?!), but I clearly felt a pull in that direction, and am glad I listened to it.

Can you tell us a story about the hard times that you faced when you first started your journey?

I started my first business two years out of undergrad, with almost no operating experience. I had spent two years in venture capital, and thought I knew the secrets of starting a great company. Boy was I wrong. It turns out that VC trains you to judge businesses well, but building one from scratch is another can of worms entirely. I picked the wrong idea, didn’t have the right founding team in place, didn’t raise enough money, and ended up falling flat on my face. At the time it was incredibly painful, since it was the first time I’d really failed in my life. In retrospect though, that experience was an enormous gift. I would have made all those same mistakes the first go-around whether I was 23 or 33, so it was good to get them out of the way, and to learn to get back up from a big fall and keep marching.

Where did you get the drive to continue even though things were so hard?

You know, I wasn’t planning to start another business for a good long while after that first failure. But life had other plans. During my time in business school after my first startup, some friends and I came up with the idea for Skylight, and the reaction to it was really strong compared to anything else I’d come up with before. Of course now with the benefit of hindsight it all seems obvious to me, but at the time the idea of building a digital picture was pretty strange. Still, I saw the customer reactions, and knew there was something special here. So I refused to let go, running it nights and weekends for four years! Finally, at some point, it had grown so large and profitable that I could afford to leave my job and pursue it full time. So you could say I hacked my way to getting confident enough to do another venture, by nights-and-weekends-ing it until it became a no-brainer.

So, how are things going today? How did grit and resilience lead to your eventual success?

Today, we have an awesome team of 15 people in the US and a team of 25 in the Philippines. We serve hundreds of thousands of families each year, who love our products with a passion (which is incredibly rewarding). At this point, Skylight has a life of its own, and I see our job as bringing this wonderful innovation we were lucky enough to discover into as many families’ lives as possible.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

The first 40 Skylights we ever made were done on a dorm room floor — we wired, we sautered, we glued, etc. It took an insane amount of time, wildly unprofitable, but we were so proud at the end of it to have made these working devices. So then, in true lean fashion, we put them on sale and saw what happened. And guess what — they sold out! Hooray! The problem was that a bunch of business school students were never going to produce an A+ quality hardware product, AND many of the people who purchased those first 40 were the most successful people in my network, who were kindly trying to support me. So we basically sent out a bunch of duds (not all, but many!). Fortunately, I think they’ve all forgiven me at this point 🙂

What do you think makes your company stand out? Can you share a story?

It’s for sure our culture. We only have 15 full-time team members in the US, and are able to accomplish enormous amounts as a tiny team. Part of it is just hiring smart, passionate, hungry people, but it’s also the values we live at this company that enable those talented folks to succeed.. We have three ironclad values — — Autonomy, Rigor, and Care — — and we talk about them all the time, to ensure that when crucible moments arrive, we actually live by them. Those moments might be saying no to hiring someone who is compelling but kind of a jerk. Or in showing care to someone who is struggling with their work, or even in their personal lives, by having the patience to guide and coach them, and give them the space to grow. Or in being able to give candid but kind feedback, to a subordinate or a superior, to improve a process or overcome a communication challenge. This all sounds like cliche stuff, and many companies purport to have values like these, but the actual hard part is to go beyond fluffy language and (a) know which values are actually authentic to you vs. not, and (b) put in the effort to live by those values day-to-day.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

I think burnout is something that many if not most CEOs grapple with regularly. I know some founders whose energy is seemingly limitless, but will freely admit that I’m not one of them. My energy goes up and down all the time, sometimes related to the company’s progress/setbacks, but sometimes seemingly independent from that. The best tools I’ve found for combating burnout are (1) surrounding myself with energy-giving colleagues and advisors, (2) taking real vacations a couple times a year, and (3) being honest with myself about which parts of my job give me energy vs. take energy, and trying to structure my role to do more of the former and less of the latter.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

This company would not exist without many people’s passionate efforts. But I have to say the biggest thanks goes to my business partner Ricardo Aguirre, because his contribution came at such an early pivotal moment. When I was the only one who had the time and energy to drive Skylight forward back in 2014, he saw something special in the idea, and in me, and came onboard. For 3–4 years after that, we worked nights and weekends to keep this business going, somehow managing to work well together and enjoy each other’s company the whole time. It’s not easy to find someone like that, and I’m very thankful to have found Ricardo. And perhaps that gave me a taste for what great colleagues can do for your business and your wellbeing, because we’ve managed to hire a number of similarly remarkable people since who have changed the course of the business in so many ways.

How have you used your success to bring goodness to the world?

I’m a firm believer that it’s possible to have a company that does good for the world and makes money. Not every company can do both, but if you can, it’s really very special. And I think Skylight is a great example of that. Every Skylight that goes out from our warehouse ends up helping a family to better connect and share love with one another. That’s hundreds of thousands of families each year we are able to touch, and bring closer together. I don’t think any amount of charitable work we could do would rival the amount of good we’ve been able to do just by shipping Skylights into the world. And that’s all been enabled by having a profitable business model, which has made us sustainable and allowed us to scale extremely quickly.

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

-The “people stuff” is always the hardest. When people get upset at you (or vice versa), it can be so energy draining. Conflicts will arise, but life is always better with more communication, assumptions of good intent, etc.

-Get used to outsiders not believing your idea, and don’t take it personally. I still get somewhat irked when people think that Skylight is just a picture frame, and ask what happens when this product fad is over. No, I want to shout! Skylight is a platform for family sharing, no different from WhatsApp, Instagram, etc. It’s not going anywhere! But the truth is these things that might be obvious to a founder/CEO who lives and breathes them are not obvious to outsiders, and there’s no need to be frustrated about it.

-There will be crises that feel existential, but most crises will calm with enough time. We’ve had some doozies, from cash crunches to supply chain issues. But things that feel terrifying at the time tend to blow over within a few days or weeks, so you just have to remember that the fear is fleeting, and trust that the business will get through it.

-Building a great culture is an incredible asset. I go into more detail on that above.

-The best thing you can do for an employee is to empower them. Yes, I have a tendency to micromanage. Don’t most of us? But I’ve come a long way in seeing the almost miraculous things that happen when you give someone the autonomy to really own their work.

If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I am fascinated by the power of unexpected kindness, aka “kindness when it’s hardest to be kind.” There is nothing more gratifying, or instantly connection-building with a fellow human, than when you find an opportunity to show someone kindness when none is expected. The most powerful moments of kinship can happen when you show unexpected kindness to an adversary. As humans we have a natural tendency to be tribal: to fight over small issues with family members, to get into furious arguments with coworkers we perceive as having slighted us, to think that neighbors doing something annoying are terrible people. We tend to retreat into our respective corners, assume the worst, and end up in seemingly irreconcilable conflicts. (yes I’m partly referring to US politics in 2020, but it also happens all the time in our daily lives).

I’d suggest that in cases like that, the most powerful way to forge a bond with someone, to heal a rift, is to reach out with humanity when the other person isn’t expecting it. Enemies can become friends, rifts can heal instantly, when you extend a hand to someone.

If everyone found one opportunity each week to do one act of unexpected kindness, to a stranger or even an adversary, the world would instantly be a much better place! Can we make a movement around this, please? 🙂

How can our readers follow you on social media?

Twitter: @michaelsegal

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