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Confessions of a Serial Entrepreneur–And 7 of His Best Pieces of Advice for Being a Better Person

Show up. Judge less. Build deep connections.

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BY Glenn Leibowitz - 29 Jun 2018

CREDIT: Noah Kagan/YouTube

After a stint as employee #30 at Facebook, Noah Kagan left to become the founder and "Chief Sumo" of two successful internet companies:, a cloud-based app used by hundreds of thousands of websites to collect email addresses; and AppSumo, which offers group discounts on digital products and services.

He's also a prolific blogger and the host of an excellent podcast on which he interviews startup founders and shares some of what he's learning from his own entrepreneurial journey.

He recently returned from an "epic" week-long retreat in Israel, Reality Tech, which is described on its website as an "energizing leadership development journey ideal for entrepreneurs, influencers and visionaries in the tech space."

In a recent short episode of his podcast--or "minisode," as he describes it--Kagan shares seven things he learned about himself from the retreat:

1. Show up.

Kagan makes a confession here: "Sometimes for work, I haven't been showing up for my company...That's not how I want to be."

His advice? "Don't do the bare minimum. Commit with your work. Commit with your self. Commit with your relationships."

"Have you ever done something where once you did it you were like, 'Yo, that was really good.' You know why? Because you showed up."

2. Judge less.

"I don't know about you but I am insanely judgmental," admits Kagan.

He describes meeting a bald-headed Portuguese woman. Setting aside the stereotyped impressions he formed of her before he had even met her, he made a point of approaching and speaking with her. "And, lo and behold, Barbara became one of the favorite people I met on the trip."

"So the people, groups, co-workers, others you don't like...go hear them out-- and then be super-judgmental. Think of everyone as black and white and give them a chance to fill themselves out with color."

3. Plan your growth.

A conversation with a rabbi led him to explore the topic of personal growth. "Ask yourself, 'What is growth?' How are you better now than in the beginning of the year? That's growth."

"If you don't know what growth looks like, you can't actually do it. Think about where you want to be at the end of this year...Ask yourself, 'Am I on track? And what do my personal, my work, and my workout goals look like for this year?'"

4. Be open to change.

Kagan describes meeting his first Palestinian, an encounter that, like his meeting with the bald Portuguese woman, smashed some of his long-held misconceptions.

"For yourself, when you're anti-something, or you're just waiting to respond to an argument, are you really open to hearing another point of view? And are you really...trying to understand the other person?"

"If you want to be open-minded and you want to be open to change--because it generally makes life a little better and more flavorful--maybe try to hear other people out."

5. Create space.

"Normally in your day job, like mine, you're working...and so it's hard to actually make that time to think about these things in life, like what I am trying to in the future, how am I trying to be growing?"

"What was interesting about space is that [Reality Tech] created that for us with some of the questions--a framework--and just time to think about it."

"For yourself maybe it's five to ten minutes in the morning, or maybe it's ten to fifteen minutes on the weekend, ask yourself, 'What does my great life look like? And what is holding me back from that?'"

6. Be a man (or woman) of your word.

Kagan briefly shares the story of David Ben-Gurion--one of the founders of modern Israel and the new nation's first prime minister--and his commitment to living in the desert, despite the obviously harsh conditions. For Kagan, Ben-Gurion's bold move was a perfect example of living by example.

Learn from this, Kagan suggests: "If I say I'm going to do something, if I say I'm going to be somewhere, if I say I'm going to act on something, I'll do it. If you say you're going to call someone, call them. If you say 'I'm going to follow-up with you,' follow-up."

7. Build deep connections.

Kagan describes the incredible variety of people he met on the retreat, and the intense conversations he enjoyed with them: "Guys who had sold multiple businesses, a vice president from Nike, a dude who hung out with the Pope...I had literally never had such consistently deep conversations with this many people in many years."

"When is the last time you had a really great conversation? Create or put yourself in places to have those conversations. Go to certain events. Maybe find new friends, or go back to the friends where you generally have those types of conversations with. Think about the people that you're around."

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