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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.

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:

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Have a listen!

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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

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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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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.

This year, be as happy as these old ladies packing up #Beatles #RubberSoul! Get the standard or mono vinyl now! https://t.co/5gAcjQzzdZ pic.twitter.com/nP4sBHQb84

— The Edit Vinyl (@Vinyledit) January 2, 2017

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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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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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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https://youtu.be/XuH_iaANSq0

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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.

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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Steve Murch

Steve Murch is a smart, humble and motivated guy who’s had an incredible run in tech.

Back in 1991 — after he’d done all the school (Carnegie Mellon, Stanford, and HBS) — he was part of the initial Access team at Microsoft, launched their first online multiplayer games (zone.com), and after leaving founded VacationSpot (think HomeAway) with Greg Slyngstad — which they sold to Expedia in 2000. While at Expedia he led the Vacation Packages business, and helped revolutionize the way people buy travel.  He was also the Chairman of Escapia for five years, and has been a lecturer at UW’s Foster School of Business.

Faced with the grim prospect of early retirement or staying in the tech mix, he focussed on getting back to crafting software, eventually leading to BigOven…a recipe db/meal planner with more than 12M downloads.

In this episode we talk a lot about food, how tech can impact the planning and yes, cooking of meals, and what techs like machine learning and Echo may mean for how people behave in the kitchen and store.

Food waste and families eating together are both important priorities for BigOven, and Steve provides compelling evidence for why. Just one data point: it was found that eating two meals as a family per week was the only variable that could be correlated with being National Merit Scholars. (!)

As mentioned in the show…check out the 1956 vision of computers in the kitchen starting around 25 seconds in:

Tesco’s Virtual Supermarket in Korea (Photo credit: designboom)

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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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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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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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