@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 2.3: Matt Revis, VP Product, Jibo

As they say, hardware is hard. Matt Revis -- a veteran of the speech recognition wars at Nuance, and now VP of product at robotics startup Jibo -- is no stranger to this. Getting various software keyboards and versions of Dragon shipped by OEMs on hundreds of millions of handsets (smart and no so smart) takes a willingness to grind, and Matt has that in spades. Good thing too because he's jumped into an exploding segment -- intelligent home devices -- with relentless, well-funded competitors who have platforms and data that provide quite a moat. Jibo is taking a different approach than, say, Echo or Google Home. They believe an anthropomorphic little robot, tuned to interact and genuinely connect with different members of the family, is a differentiated play versus static appliances with disembodied personas (Alexa, Google Assistant, etc.). Much of this strategy is based on research done by Cynthia Breazeal, the magnetic robotics star who pioneered this work at MIT's Media Lab before its spinout into Jibo. Both Matt and Steve Chambers (Nuance's dynamic #2 for years) have signed up to help Cynthia bring the little robot to market.
Matt Revis, VP Product, Jibo

As they say, hardware is hard. Matt Revis — a veteran of the speech recognition wars at Nuance, and now VP of Product Management at social robotics startup Jibo — is not someone to shy away from a tough challenge.

Getting various software keyboards and versions of Dragon shipped by OEMs on hundreds of millions of handsets (smart and some not so smart) takes a willingness to grind, and Matt has that in spades. Good thing too, because he’s jumped into an exploding segment — intelligent home devices — with relentless, well-funded competitors who have platforms and data that may provide quite a moat.

Jibo is taking a different approach than, say, Echo or Google Home. They believe a slightly anthropomorphic little robot, tuned to interact and genuinely connect with different members of the family, is a differentiated play versus static appliances with disembodied personas (Alexa, Google Assistant, etc.). Jibo is all about being relatable, and funny, and someone you’re invested in as they “grow”.

Much of this strategy is based on research done by Cynthia Breazeal, the charismatic robotics star who pioneered this work at MIT’s Media Lab before its spinout into Jibo. Both Matt and Steve Chambers (Nuance’s dynamic #2 for years) have signed up to help Cynthia bring the little robot to market.

It won’t be easy. The tech (think Alexa strapped to an Echo that moves in place but also has facial recognition and a display) has a lot of surface area where the table stakes are moving very quickly. And once they’ve figured all of that out, then they need to build and sell it.

But Matt (and Steve) believed in speech-based personal assistants years before Siri, and if anybody can do it they can. In this episode, Matt and I discuss many of their challenges, their unique approach, and how they doing. It’s “the hardest thing I’ve ever done, and the most fun — both by a lot”, and you’ll hear the authentic voice of the entrepreneur.  Have a listen to the podcast, but also watch the Jibo Program Update below, which gives you a sense of the V1.0 product, but also of how the business is managing the expectations of a community eager to get its hands on the guy.

Here’s a snippet from the full podcast:

 

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@techvitamin 2.2: Greg Gottesman, Pioneer Square Labs

Greg Gottesman, Managing Director
Greg Gottesman, Managing Director

Much has changed about Venture Capital in the last few decades, and Greg Gottesman has witnessed it up close and personal as a founder of Madrona Venture Group, then of Madrona Labs, and now of Pioneer Square Labs (PSL). And while he’s still involved at Madrona, PSL is part of a clear evolution towards the entrepreneur, and getting closer to the initial creative process in a startup.

Greg’s widely known as an entrepreneur’s entrepreneur, with a strong sense of product, and great empathy for what founders go through. At Madrona Labs, he experimented with the notion of a venture firm providing the space, talent and financial resources to get founders off the ground, and through the first brutal filter.

Greg Gottesman and Geoff Entress lead Pioneer Square labs
The Pioneer Square Labs team (photo credit: Geekwire)

Now at Pioneer Square Labs — along with one of the country’s most quietly successful angel investors, Geoff Entress — Greg has taken the lab model even further, tweaking some of the early formulas at Madrona, and bringing a host of top tier VCs to the table for the entrepreneur. If you’re an aspiring Founder, PSL will quickly put you in close proximity to engineers, designers, and a broad group of investors who are ready to provide both capital and hands-on help. PSLs “limited partners” aren’t passive pension funds, they are top VC like Greycroft.

In this episode, Greg and I talk about entrepreneurship, the new model they’re trying to drive, the kind of people he’s hoping will walk through their front door.  Have a listen.

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@techvitamin 1.8: James Siminoff, CEO/Founder of Ring.com

When Shree and I first met Jamie Siminoff, he was the Founding CEO of a cool little company called Simulscribe, which turned voicemail audio into text. He was a tough competitor with a great sense of humor, and had enough perspective to know that startups are hard, and that a few shared beers and laughs break up the insanity very nicely. We also had a common competitor that provided no end of hilarious material: the overfunded, infamous, and batshit-crazy Spinvox. Jamie's latest venture -- Ring -- is also his most colorful successful, now with 400+ employees, world wide offices, and nicely growing sales.
James Siminoff

When Shree and I first met Jamie Siminoff, he was the Founding CEO of a cool little company called Simulscribe, which turned voicemail audio into text.

He was a tough competitor with a great sense of humor, and had enough perspective to know that startups are hard, and that a few shared beers and laughs break up the insanity very nicely. We also had a common competitor that provided no end of hilarious material: the overfunded, infamous, and batshit-crazy Spinvox.

Jamie’s latest venture — Ring — is also his most colorful and successful, now with 400+ employees, world wide offices, and nicely growing sales.

Never one to be conventional, he had a company-saving appearance on Shark Tank (see below). Running on fumes at the time of the taping, he didn’t get a take-able offer, but got enough publicity from the episode to generate millions in revenue, and get the company — then known as Doorbot — over the hump.

Jamie Siminoff on Shark Tank

Ring is conceptually simple: it’s a video doorbell that records and sends video of what’s going on by your front door to wherever you are. Designed to thwart bad guys, a Ring sometimes picks up other critters:

Of course, there’s nothing simple about startups, especially hardware. We talk about his growth, the tradeoffs he makes, how he continues to let his mission shape very basic decisions in the company. Jamie is the middle of the IoT battle, and has super well informed opinions about home hubs, Alexa v. everybody, and much more.

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Uber is doing awesome things all over the world, and tech hub Seattle has been a great test bed for the company's new service offerings. But it hasn't been easy. Brooke Steger, Uber's GM for six states in the Pacific Northwest has in just under four years worked through controversy over business models, regulation, safety, aggressive driver recruiting tactics, bad press for their Founder, and more. She's also helped introduce her region to UberEats, UberPool, UberHop (yeah I know, what's that?!), scholarships for drivers, and more.

@techvitamin 1.6: Brooke Steger, GM of Uber

Uber is doing awesome things all over the world, and tech hub Seattle has been a great test bed for the company's new service offerings. But it hasn't been easy. Brooke Steger, Uber's GM for six states in the Pacific Northwest has in just under four years worked through controversy over business models, regulation, safety, aggressive driver recruiting tactics, bad press for their Founder, and more. She's also helped introduce her region to UberEats, UberPool, UberHop (yeah I know, what's that?!), scholarships for drivers, and more. We dive into Uber topics both globally, and some Northwest specific things. Ever wonder where all those black cars were hiding before Uber, or how much a driver can make in an evening?
Brooke Steger, GM of Uber

Is your UberX car going to smell like the last Chicken Tikka delivery it just made for UberEats?

Do I now have to tip? That was a key part of the magic.

Uber is doing awesome things all over the world, and tech hub Seattle has been a great test bed for the company’s new service offerings.

But it hasn’t been easy. Brooke Steger, Uber’s GM for six states in the Pacific Northwest has in just under four years worked through controversy over business models, regulation, safety, aggressive driver recruiting tactics, bad press for their Founder, and more. She’s also helped introduce her region to UberEats, UberPool, UberHop (yeah I know, what’s that?!), scholarships for drivers, and more.

We dive into Uber topics both globally, and some Northwest specific things. Ever wonder where all those black cars were hiding before Uber, or how much a driver can make in an evening? How is Uber partnering with Seattle Metro transit to reduce commute transit times.

How should Uber’s entrance into Seattle been handled differently (if it should have been)?

Brooke’s story is compelling. A UW grad, she took some time to teach Physics and Computer Science to kids in Mexico, she jumped into tech via a Craigslist ad and has never looked back.

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@techvitamin 1.4: Ford Davidson, Founder/CEO of Coolr and Dashwire

Shree joins me as guest host for this episode with Ford Davidson, a born entrepreneur who in the little more than a decade since he's been out of college, has been a fast tracked Product Manager at Microsoft, founded and sold Dashwire to HTC, worked his earn out by building a global product organization, and started another company, Coolr...which he's recently wound down. Ford has a badass twitter handle too: @blackball.
Ford Davidson, Entrepreneur

Shree joins me as guest host for this episode with Ford Davidson, a born entrepreneur who in the little more than a decade since he’s been out of college, has been a fast tracked Product Manager at Microsoft, founded and sold Dashwire to HTC, worked his earn out by building a global product organization, and started another company, Coolr…which he got funded, but has recently wound down. Ford has a badass twitter handle too: @blackball.

Ford is a creative force, and easily one of the most enthusiastic product people I know. His trademark “sweeet!” is generously given to other people’s ideas and product, and he remains one of the more humble home-run hitters out there.

Failures can be powerful growth experiences, and I’m sure Ford will benefit from having stepped up to the plate again. Coolr was inspired by the idea that organizations operate better when employees know what’s going on, and when managers connect with their teams. Ford gives a candid assessment of what they did well and didn’t, the role that investors played in timing and roadmaps, and what they’d do differently.

We contrast Coolr with Slack’s funding and development path — $10M of investment, zero revenues, and a huge pivot, before the current, glorious product emerged.

But we also talk about best practices org info flow at Google, Amazon and Microsoft, “holocracies”, why apps like TinyPulse work and sometimes don’t, and more. If you want to be a manager today, you’d better be ready for more transparency — and more data driven assessment of your performance — than ever before.

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@techvitamin 1.3: Kristen Hamilton, Founder/CEO of KORU on talent, women in tech, and making the leap

Kristen Hamilton Founder/CEO of KORU
Kristen Hamilton, Founder/CEO of KORU

If you’ve thought at all about what you’re buying your kids in a college education, or how the job market is going to evolve, or why companies like Google are looking far beyond the Ivy League for talent, or why female HR execs don’t magically fix pay gaps, or why companies are beginning to split strategic talent management and HR into separate functions, or, or… this episode is a great listen.

Is it time to “Disrupt the degree”? Is free college attendance a good idea if the system doesn’t change. Do you want to put your federal tax dollars to work on a system that can’t seem to control its costs? Should so many people go to college, or should we be thinking more about training people for jobs that don’t necessarily require a college degree, as explored in this NYT piece.

I’ve known Kristen Hamilton for over ten years, and she’s always been wicked smart, refreshingly pragmatic, and full of insights and turns of phrase that make the time fly. Happily, in this episode I talk very little, because you’ll hear very quickly that what Kristen says is information rich, fascinating, and truly strategic.

I didn’t know what it was called officially, but in talking with Kristen, I discovered the term “Entrepreneur Imposter Syndrome” (thank you Dan Shapiro) … the gut feeling that you don’t know what you’re doing and everybody’s about to find out? Ever experienced that? I certainly have.

We talk a lot about the “KORU 7”: not a TV station, but the success traits they’ve discovered at KORU — the company she founded in Seattle — which is trying to give recent college grads essential job skills. Kristen’s of course not new to the startup game, but KORU has raised more than $13M from top tier VCs like Andreessen Horowitz, Battery Ventures and Seattle heavyweights Maveron and Trilogy. We go into depth on what KORU’s up to, how they’re doing, and I think you’ll find it inspiring.

Note: we had some bandwidth issues, especially late in the recording, so there are some places where the sound isn’t stellar, and where bizarre Skype noises have been cut out. Apologies.

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@techvitamin 1.2: Former Swype CEO Mike McSherry and Sundar Balasubramanian on Healthcare Tech

Mike McSherry
Mike McSherry, Entrepreneur

This episode ranges pretty far afield. It’s mostly about healthcare tech of course — because that’s what Mike and Sundar are spending their time on right now. But they are serial — and very successful — entrepreneurs and have a unique perspective on tech, entrepreneurialism, and what might work. They’re pretty fearless.

Mike in particular has picked and created winners in radically different domains: he’s founded phone companies (yes, plural), and a company that sells embedded device software. Shree, who joins the episode as a guest host, has long had an interest in healthcare tech.

After having sold their startup Swype to Nuance for $100M, Mike, Sundar and Aaron Sheedy eventually moved on to figure out the next thing. The first post-Nuance project involved rocket propelled drills. This is discussed in the podcast, and happily, they didn’t incinerate themselves in the basement of a UW building.

They are now EIRs at Providence Health and they can pretty much explore whatever they want. Devices. Services. Prevention. Tech to reduce readmit rates. I don’t think they are developing new drugs, but they have a pretty broad scope.

In this episode we talk extensively about what they’re seeing, including new exciting new areas of innovation, things that are harder than they expected, and areas that’ve surprised them. We talk about Shree’s tow truck metaphor (which really is perfect).

One topic that I haven’t seen discussed before — though I’m sure it has been — is whether this incredible innovation will really serve those who are most sick, or those who are collectively costing the system the most. It’s one thing to be rich and have a drug cocktail customized to your genome, and another thing to be poor and sick. Is the life expectancy gap between rich and poor going to expand at a more rapid rate? Does drug innovation target the most broad causes of illnesses, or ones that have a good chance of getting paid for?

Based on what these guys are seeing, one thing seems really clear: being paid a fixed, and ever lower, amount for certain procedures is providing massive motivation for the providers to innovate cost out of the system. God bless America.

Sundar is currently an EIR at Providence Healthcare. Prior to Providence, Sundar ran product management at Swype which was his second adventure with Mike McSherry. Before that Sundar worked for Mike at Amp’d Mobile as well. Sundar has also held multiple product management roles at Qualcomm working on mobile OS’s, emerging market smartphone strategy, and mobile commerce. Sundar is a Seattle transplant, originally from California. He graduated from U.C Berkeley and has a background in Computer Engineering. He’s a backpacker, hiker, technologist, and dog-owner.
Sundar Balasubramanian

We touch on Amazon’s Echo a bit too. All of us have been involved in Speech and Natural Language processing, and this device, which is a far more disruptive factor in the market than most people know, may come to be the most surprising application of these technologies. Amazon is doubling down in a big way — as they should.

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