@techvitamin 2.7: T.A. McCann, serial entrepreneur, ex-pro sailor, on healthcare tech and grinding it out

If you're competing with T.A. McCann in the startup world, know that he's raced around the world in boats, in horrible conditions, and has probably surrounded himself with people who, like him, will not complain because they enjoy the grind -- after they've been strategic and have arrived at the race with the tools to win. Which he's done. A lot.
T.A. McCann

If you’re competing with T.A. McCann in the startup world, know that he’s raced around the world in boats, in horrible conditions, and has probably surrounded himself with people who, like him, will not complain because they enjoy the grind — after they’ve been strategic and have arrived at the race with the tools to win.

Which he’s done. A lot.

T.A. was the Founder and CEO of Gist, which he sold to Research in Motion in 2011. He’s also a relentless contributor to the Seattle startup scene, whether as part of TechStars or Startup Weekend, as an Angel investor or now as an Entrepreneur in Residence at Providence.

It’s fun to talk about sailing as a metaphor for the startup life. The parallels are clear, and being a member of an Americas Cup crew, and working with Larry Ellison so closely, is such rarified experience that it’s worth covering a bit, which we do.

If you're competing with T.A. McCann in the startup world, know that he's raced around the world in boats, in horrible conditions, and has probably surrounded himself with people who, like him, will not complain because they enjoy the grind -- after they've been strategic and have arrived at the race with the tools to win. Which he's done. A lot.
T.A. McCann’s boat in the Americas Cup

Outside of sailing, we cover a lot of ground, including his investment theses (data, mobile, and being attracted to things he himself would find useful); how to get healthcare tech into the hands of populations that need it but maybe can’t acquire or use it easily (old or poor or both); whether the insurance industry would completely subsidize the distribution of smart devices, say, if it led to better outcomes; whether the AI Doctor is more of a stand alone “entity” or whether it’ll mostly augment.

Here’s a clip of T.A., talking about the types of people and ideas he’s looking to meet and potentially invest in or collaborate with:

Have a listen!

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@techvitamin 2.6: Lauren Woodman, CEO of NetHope

This episode is mostly about doing great work in difficult places for people who really need help. Fundamentally that's what Lauren Woodman and her NetHope team do. It's not about speech recognition, AI (yet), or your wifi fridge telling you via OCR that your milk is about to sour.
Lauren Woodman, CEO of NetHope

This episode is mostly about driven professionals doing great work in difficult places for people who really need help. Fundamentally that’s what Lauren Woodman and her NetHope team do. It’s not about speech recognition, AI (yet), or your wifi fridge telling you that your avocado ice cream is about to melt.

We talk about providing connectivity in giant, semi-permanent refugee camps, and about streams of migrants — otherwise educated and smartphone carrying people trying to live their lives — and giving them basic services that of course we’d crumble without. A constant thread: having the grit to work through solutions in places where the environment (physical and political) is potentially hostile. They do work that’s super tangible (getting satellite dishes up), and work that’s less so (data security policy so refugees are protected even in cyberspace). It’s applied, 100% non-frivolous tech.

The Dadaab Refugee “Camp”

There are many things to admire about Lauren, not least that she’s so effectively made the transition to the world of development from tech — a culture not known for patience or diplomacy. She and her team inhabit a space between governments, and a truly who’s who set of partners, including non-profits, massive NGOs, and tech giants (The Bill and Melinda Gates Foundation, Path, Google, Microsoft, Facebook, Cisco, Dell, etc.).  This snippet gives you a sense for how crisp Lauren is about her very unique organization

NetHope is constantly on the lookout for how to operate more efficiently, both in terms of making their partners’ funds go further, but how to scale, including running training programs — NetHope Academies — so they can get abundant local human resources spooled up. The next frontier is using data in ways that were never before possible.

Lauren’s a Smith College and Johns Hopkins SAIS grad who’s on the front line of some of the world’s most painful humanitarian situations, and she’s well worth the listen.

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@techvitamin 2.5: Dave Cotter, CEO of Reply Yes

Dave Cotter is one of those people who is deceptively sunny. Sure he's engaging and funny, but you figure out pretty quickly that he's juggling something complex, really ambitious, and that he has a deep pool of that essential founder's gift: faith. He's no babe in the startup woods, and is an Amazon and RealNetworks vet. Reply Yes, Dave's current venture, is a mix of retail savvy and messaging and AI, and is at the center of what is being called "conversational commerce". They've launched two messaging centered "stores" -- The Edit, for vinyl records, and Origin Bound, for graphic novels -- where the simplicity of the offering belies a tremendous amount of tech and logistics and painstaking attention to the customer.
Dave Cotter, CEO of Reply Yes

Sure Dave Cotter’s engaging and funny. But you figure out pretty quickly that in Reply Yes he’s juggling something complex, really ambitious, and that he has a deep pool of that essential founder’s gift: faith. It’s not denial, just bedrock confidence. No babe in the startup woods (he was a co-founder of SquareSpace), he’s also done the larger company thing at Amazon, Zulily and RealNetworks.

Dave’s current venture is a mix of retail savvy and messaging and AI, and is at the center of what is being called “conversational commerce”. Inspired by the sheer simplicity of text, and to some extent by what’s been going on in China with WeChat’s platform, Reply Yes — and a host of other startups (Magic, x.ai, Peachd.com, etc.) — has been running hard at this problem for the past few years.

Dave’s team has launched two messaging centered “stores” — The Edit, for vinyl records, and Origin Bound, for graphic novels — where the simplicity of the offering belies a tremendous amount of tech and logistics and painstaking attention to the customer. The company is a product of Madrona Venture Group’s labs, and in December raised $6.5M in a Series A — bringing their total to $9M.

In this episode we talk about what he’s done to get Reply Yes going, how they’ve managed to focus, and navigate the crazy world of music brands, while fundamentally innovating at the edge of natural human interfaces and offer personalization. How does he as CEO make tradeoffs between going very deep in vertical specialization, yet keeping an eye on the big platform play?

While Reply Yes came out of the gate with a text message centered product, since that time Facebook, Microsoft, Apple and others have made messaging — and in particular transacting over messaging — a much greater focus. We talk about how they are navigating this…dancing with goliaths, but taking advantage of the tech they are providing at the same time. A classic entrepreneur’s dilemma.

Have a listen.

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