Keep Going

28:38

What do you do when it’s time to retire and, well,...

Keep Going ·

2026/10/05

What happens when you reach the end of a successful career and realize you’re not done working?On this week’s Keep Going, I talk with Alan Wexelblat, a longtime software engineer, UX leader, startup veteran, and MIT Media Lab alum who retired earlier this year. Instead of settling into retirement, Alan began volunteering full-time with organizations supporting immigrants and refugees.We talk about why he made that choice, what decades of building software taught him about failure, and why he thinks

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28:18

Perseverance pays

Keep Going ·

2026/09/28

What happens when a product takes ten years to become an overnight success?On this week’s Keep Going, I talk with Reid Robinson, founder of Robinson Exotech Corp. and creator of the X Leg, a wearable exoskeleton designed as a hands-free alternative to crutches. The idea came out of Robinson’s own recovery after a serious car crash in 2015 shattered his lower leg and ankle. Over the next two and a half years, he went through 13 surgeries while doctors tried to save his leg.Between surgeries, Robinson

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27:50

From a little red suitcase to a billion-dollar company

Keep Going ·

2026/09/21

What happens when you finally get everything you thought you wanted, and realize you want something else?Joe Spector came to America from the Soviet Union at ten years old. His family arrived with $100 each. Joe had a red suitcase.He studied his way into Berkeley, finished in three years, and landed a job at JP Morgan. It was the kind of secure, prestigious career his younger self thought meant he had made it.Then he realized he didn’t care about it.Joe left finance, moved into startups, and

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30:29

Scott Jordan built a brand and a million dollar...

Keep Going ·

2026/09/14

Note: The video portion of the interview failed so this is an old-fashioned audio podcast. Scott is a great guy so I wanted to share this regardless.What does success look like after 25 years in business?On this episode of Keep Going, I talk with Scott Jordan, founder of SCOTTeVEST and self-described “Chief Pocket Scientist,” about building a clothing company around a simple idea: people carrying a growing pile of technology needed somewhere to put it. Long before the iPhone, Scott was making vests

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37:02

How to build something as successful as the Apple Store

Keep Going ·

2026/09/09

Ron Johnson built the Apple Store, then watched the world copy it for two decades. In this episode of Keep Going, he walks through how that happened, starting with a choice he made early on: learn retail from the ground up, not from a spreadsheet. After Harvard Business School, he went to unload trucks in a Mervyn’s store, then rose through Target during its big 1990s run, where he helped push “design for all.”Ron is the author of an upcoming book, Shop Different, which is in pre-orders now. We got

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6:23

How psychedelics changed my life

Keep Going ·

2026/09/08

This one is personal.I started working on Shroomies in 2018, after my dad died and I entered one of the darkest periods of my life. I was depressed. I was taking SSRIs. I was very close to self-harm. I didn’t feel like myself, and I didn’t know how to get back.Then a friend invited me to a psychedelic mushroom session.I thought it sounded ridiculous. I’m not a Burning Man guy. I’m not a hippie. I don’t like the Grateful Dead. I definitely don’t like Phish.But I went.What happened over the next six

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32:04

A top-tier product manager tells us how to survive...

Keep Going ·

2026/08/31

Melissa Mohr spent 13 years at Amazon. She helped build Amazon’s Canadian toy business, worked on the company’s early push into online groceries, and then spent about nine years working on Alexa and the smart home. Today, she’s SVP of Product at Vivint.None of that was part of some carefully mapped career plan.Mohr studied animal science in college. She expected to spend her career working with horses. Instead, she ended up helping solve some of the strange problems that come with trying to change

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14:00

Inside iWallet, the payment platform for contractors

Keep Going ·

2026/08/04

Jim Kolchin started iWallet because he knew the problem from the inside.Before he was building fintech software for contractors, he was a contractor himself. He started his first business in 2003, spent 15 years working in the field, and grew that business from nothing into an eight-figure company. That is where he saw the pain around checks, credit cards, receivables, and all the little financial tasks that slow down home service businesses.Kolchin describes iWallet as a new way for contractors to

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35:32

Making art out of pain

Keep Going ·

2026/08/03

Angie Elita Newell does not write easy books.Her novel, All I See Is Violence, is not a fantasy escape, which she joked about after finding herself surrounded by “sexy fairy” books at BookCon. It is a historical novel built from trauma, archival research, Indigenous memory, and the long shadow of state violence.Newell is a member of the Liidlii Kue Nation, part of the Dene linguistic group. Her mother was an Air Force pilot. Newell became a historian. Those facts sit close together in her life, but

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26:45

The internet didn’t kill magazines. We did.

Keep Going ·

2026/07/27

I had one of my favourite conversations in a long time this week with writer and Full Bleed podcast host Arjun Basu.We both came from the magazine world. We remember the days when magazines had millions of readers, editors could call a trend before it happened, and entire industries waited to see what would appear in next month’s issue.Then the internet arrived.Most people tell that story as if technology simply destroyed print. Arjun had a more interesting take.He argues the first mistake wasn’t

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28:27

Creators aren’t the new influencers, they’re the new...

Keep Going ·

2026/07/20

When most people hear the word “creator,” they think of someone promoting protein powder or the latest gadget. Tanya Cohen sees something very different.Cohen is the co-CEO of Made By Us Studios, a company trying to bridge Hollywood and the creator economy. On this week’s Keep Going, she made a simple point that explains why so much of the media business is changing.“Every creator can become an influencer, but not every influencer can become a creator.”That distinction matters.An influencer rents

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16:47

Shutting down a business: What every founder needs to...

Keep Going ·

2026/07/13

Starting and running a business can be one of the most rewarding experiences, but knowing when and how to shut it down is equally crucial. In this post, we’ll explore key insights from Dori Yona, CEO and co-founder of Simple Closure, on navigating the often daunting process of business closure. You’ll learn about the common pitfalls, best practices, and how to ensure a smoother transition during this challenging time.This was an interesting interview and had a lot of info for folks who might be

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16:47

Why good is not enough

Keep Going ·

2026/07/06

Keith Wyche has had the kind of career that looks clean from the outside.Bell. IBM. Pitney Bowes. Grocery. Walmart. Board seats. Books. Big jobs. Big teams. The sort of resume that makes people assume there was always a plan and that the climb was smooth.It was not.Wyche told me something on Keep Going that I think a lot of ambitious people need to hear. Early in his career, he was getting results, but he was not getting promoted. He was young, talented, and frustrated. So he gave his boss an

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14:52

WorkClaw wants to build an AI team for your team

Keep Going ·

2026/07/01

Everybody has heard the promise by now. AI is going to save time, reduce costs, and help businesses get more done. The problem is that most people still don’t know where to start.That’s the challenge Will Ruben is trying to solve with WorkClaw, a new product from Workmate Labs that turns AI agents into something closer to digital employees.Ruben describes WorkClaw as “an AI team for your team.” Instead of asking users to learn prompt engineering or build complicated workflows, the platform lets them

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19:49

How Lium turns physical-world data into answers

Keep Going ·

2026/06/24

Josh Knutson and Ryan Thill are building Lium for a problem that sits just outside the usual AI demo.Most AI tools are very good at text, code, and spreadsheets. Lium is focused on the messier stuff, the huge physical-world data sets that sit inside farms, climate labs, energy systems, logistics networks, and other operations where the answers are buried under terabytes of data.Knutson, the CEO and co-founder, describes Lium as an “agent harness” or a cloud operating system for agents. The idea is

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28:12

The janitor, the professor, and the meaning of success

Keep Going ·

2026/06/22

Most of us spend a lot of time thinking about what we want. A better job. More money. A nicer house. More freedom. Less stress.Very few of us spend much time thinking about what a successful life actually looks like.That question came up during a conversation with Perry Atwal, a lecturer at the University of British Columbia and author of the upcoming book Wisdom for Life. After teaching more than 20,000 students around the world, Atwal has spent years looking for patterns in the people who thrive

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14:52

WorkClaw wants to build an AI team for your team

Keep Going ·

2026/06/17

Everybody has heard the promise by now. AI is going to save time, reduce costs, and help businesses get more done. The problem is that most people still don’t know where to start.That’s the challenge Will Ruben is trying to solve with WorkClaw, a new product from Workmate Labs that turns AI agents into something closer to digital employees.Ruben describes WorkClaw as “an AI team for your team.” Instead of asking users to learn prompt engineering or build complicated workflows, the platform lets them

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14:36

How to move from the corporate world into a startup

Keep Going ·

2026/06/10

Andrew Reid has seen the supplements business from both sides, as a founder and as an operator inside a very large company, and he thinks the next step is personalisation that does not feel like homework.Reid is the CEO of Claer AI. The product is an AI-driven supplement regimen builder that asks for your health profile, matches it against a large library of peer-reviewed studies, then turns the recommendations into a practical plan, starting with sachets you can mix, and aiming later at a single

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33:24

Creative people adapt

Keep Going ·

2026/06/08

Angelo Sotira built DeviantArt at nineteen, and then spent the next two decades watching the internet grow up, get rich, and get mean. When he joined me on Keep Going, he was not doing the victory lap thing. He was trying to name what changed, and what it means for anyone trying to build something creative right now.He described the early internet as directed. People knew what was missing. They wanted communities, comments, and places to post work, and they built them from scratch because the

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13:52

The Innovators: This app makes music therapy...

Keep Going ·

2026/06/03

Most people think of music as entertainment. Rachel Francine thinks of it as infrastructure for the brain.On this episode of Innovators, I spoke with the SingFit co-founder and CEO about how her company is using therapeutic music to help people with dementia, traumatic brain injuries, and speech loss. The idea sounds almost deceptively simple. People who lose the ability to speak can often still sing. Music activates multiple regions of the brain at the same time, creating pathways that normal

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