@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 2.5: 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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@techvitamin 2.4: Soma Somasegar, Venture Partner

If one heard that someone had spent 27 years at Microsoft and then left to spend time investing in startups, you could be forgiven for thinking that it was really a form of retirement, and an opportunity to dabble. But Soma Somasegar -- who's last position at Microsoft was the Corporate Vice President of the Developer Tools division -- doesn't come across as content, or playing, or, well, done.
Soma Somasegar (Photo courtesy of Geekwire)

If one heard that someone had spent 27 years at Microsoft and then left to spend time investing in startups, you could be forgiven for thinking that it was really a form of retirement, and an opportunity to dabble.  But Soma Somasegar (@SSomasegar) — whose last position at Microsoft was the Corporate Vice President of the Developer Tools division — doesn’t come across as content, or playing, or, well, done.

In this episode we talk about his big career switch, the white hot battle in cloud computing between Google, Microsoft and Amazon Web Services, and how entrepreneurs should think about their tech stack choices.  We also talk about how Microsoft will stay relevant for another generation of developers, including embracing Linux, Python and even putting Visual Studio on MacOS.

Not surprisingly, he’s very bullish on AI, and has some interesting thoughts about how it will manifest, how humans will stay relevant, and how the different players will play to their strengths. He also talks about Madrona’s investment framework on AI and Machine Learning, and some of their experiences with Spare5, Dato/Turi (acquired by Apple), and Kitt.ai.

Have a listen.

 

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@techvitamin 1.7: Ed Lazowska, Bill and Melinda Gates Chair in Computer Science

Are our Tesla's going to band together in the Costco lot and attack us? Find out. In this episode Ed Lazowska, the eminent and long-time member of UW's Computer Science faculty joins Michael Cohen and I to discuss everything from big data, deep learning to how Universities are responding to the massive demand for computer savvy graduates. Ed's brilliant yes, but also a very animated and entertaining story teller.
Ed Lazowska, Bill and Melinda Gates Chair in Computer Science & Engineering

Are our Tesla’s going to band together in the Costco lot and attack us? Find out.

In this episode Ed Lazowska (@lazowska), the eminent and long-time member of UW’s Computer Science faculty joins Facebook’s Michael Cohen and I to discuss everything from big data, deep learning to how Universities are responding to the massive demand for computer savvy graduates. Ed’s brilliant yes, but also a very animated and entertaining story teller.

If you have children, you’ll want to listen because UW (and NYU and Berkeley and others) are doing cool things to bring computational/data fluency to programs far beyond STEM.

Other topics: the difference between knowledge and understanding in AI, and whether programmers even understand the decisions their creations are making. Crazy stuff to contemplate, and Michael and Ed are in the center of it.

A bit shorter because Comcast melted down about 2/3rds of the way in, and we lost a bit of good audio…

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