Seattle VC Profile: Leslie Feinzaig, Female Founders Alliance

When I started Ascend in 2019, I realized even though I was o-l-d OLD, I had more in common with the folks in town who were earlier in their professional investing journeys than the venerable VC’s I’d pitched as a founder. I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW

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Leslie Feinzaig is not a traditional venture capitalist. Yet she’s changing the face of venture capital in Seattle, and the country, by helping accelerate and amplify female founder talent via the Female Founders Alliance. She and her team have built a startup community of overlooked founders who are doers, not victims. Whenever I’m in a room with Leslie and any founder, I can feel and see both the support and at the same time the challenge she issues her mentees: she won’t accept anything but the best, from founders or herself, and that makes her powerful indeed.

What made you decide to be a professional investor?

I didn't decide to be a professional investor. I decided that I wanted to do everything in my power to promote and accelerate founders' success. Participating in that success is the consequence.

What did you do before FFA, and how does that benefit your founders?

I am a two time founder, and often I know first hand the journey that other founders are going through. Prior to going out on my own, I was an executive in a couple of larger/later stage startups, a product manager at Microsoft, and a strategy consultant before that. In all, I've launched and managed tech products all the way from a zero-dollar launch on my own out of my basement, to a $2B annual budget with a team of hundreds at Microsoft, and literally everything in between.

It's worth noting that all of these fancy jobs happened post-business school, which is when I moved to America. Back in Costa Rica I basically took whatever decent job I could find - like being a store manager and a call center employee. I know what it's like to come from behind and to make something of yourself against all odds.

What one company do you want to hype for us here?

Everyone should go sign up for the waitlist on datacy.com - this company will revolutionize online privacy and give power back to the hands of the consumer.

What do you think the next ten years looks like for Seattle/Pacific Northwest startups?

I look forward to a decade of ingenuity, innovation and inclusive growth. I'm excited for the roaring 20s!

What song is currently getting the most run on your Spotify/Apple Music?

I Just Can't Wait to be King, from the Lion King soundtrack. My daughters run the show at home, so our playlist is heavy on Disney tunes.

Favorite shoes?

Currently, my bedazzled Uggs boots. Comfy, warm, and sparkly.

Favorite cooking ingredient?

Cheese.

Seattle VC Profile: Ben Gilbert, Pioneer Square Labs Ventures

When I started Ascend in 2019, I realized even though I was o-l-d OLD, I had more in common with the folks in town who were earlier in their professional investing journeys than the venerable VC’s I’d pitched as a founder. I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW

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You may not know it, but Ben Gilbert is Seattle’s most famous venture capitalist. His podcast (with David Rosenthal) is the #1 technology show on Apple’s Podcast charts. The startup studio he co-founded is the most prolific in the region. His wit and his voracious appetite for knowledge make him a formidable conversationalist and incredible analyst and investor. And for all of that, he’s always had time for a novice like me, and for founders across Seattle. What’s his story?

What made you decide to be a professional investor?

I'll first answer for Pioneer Square Labs. With our startup studio, PSL Studio, we started 25 companies in the past five years. While we are super excited about the impact we're making in the ecosystem, we recognize that most companies will be started the old fashioned way, and it seemed silly to tell entrepreneurs, "sorry, we can only work with you in this one particular way." PSL Ventures exists so we can work with all great founders in the Pacific Northwest, regardless of how they chose to start their company.

For me personally, I had helped to start several companies from PSL Studio, in addition from the two earliest companies from Madrona Venture Labs (MightyAI and MessageYes, selling to Uber and Nordstrom respectively). I had also bootstrapped several mobile apps over the last decade, some of which had millions of users in the early days of the App Store. I found that my passion over time had become working with entrepreneurs to build their business rather than needing to be the one who had the idea or was running the ship.

What did you do before becoming an investor and how does that benefit your founders?

Quick Resume:

- 4 Years: Indie iOS and web developer

- 1 Year: Microsoft PM, Office for iPad

- 1 Year: Head of the Microsoft Garage

- 2 Years: Madrona Venture Labs (Worked on MightyAI and MessageYes)

- 5 Years, PSL Studio (helped start 25 companies, CEO of one for a year)

- 2 Years, PSL Ventures

- Side projects over the years: Facilitating ~30 Startup Weekends, Building 4 iPhone apps (SeizeTheDay, Zero, RedRide, ThisWeekend), building the Acquired Podcast

See below on benefit to founders.

What are your most successful investments so far?

There are a lot of great PSL companies — some that have gotten more attention than others. Keep an eye out over the next few years! :)

Why should founders want you on their cap table?

For the "me" answer, I am the co-host of Acquired.fm, a podcast that now reaches over 100,000 people a month in the technology and venture ecosystem. That comes with a few things. First, the lessons learned, both from the 150+ businesses we've analyzed, and in building Acquired itself as a business. Second, the relationships with guests and high-profile listeners. Third, the show's reach is an unfair advantage for the founders I get to work with. Of course, I also have the operating experience from helping to start many of the 25 PSL spinouts, stepping into the CEO role for a year of one of our spinouts, and building apps as a bootstrapped developer in my early twenties.

For the "PSL Ventures" answer, we aren't your run-of-the-mill VC. Our team is 25 people, most of which are engineers, designers, digital marketers, and other operational company-builders. We are actively working every day on starting new companies in the PSL Studio. It's a totally unfair superpower for early-stage entrepreneurs to have such a strong "builder" team at their back. Of course, in addition to that, my partners are also wildly talented, having started and sold multi-billion dollar companies, starting other large venture firms, and angel investing in hundreds of companies. When you raise money from PSL Ventures, you have all of us on your cap table.

How many new pitches (actual calls/zooms) do you take per month?

I would guess the number is around 10-15. But really, the goal is to do less meetings and be able to give the highest-density, earliest feedback I possibly can in a process to make the best use of a founder's time. Ideally, if I do a meeting or two with an entrepreneur, it's something I'm excited about intend to purse seriously as an investment for PSL Ventures.

How many new investments do you make per year?

In addition to PSL Studio companies (where PSL Ventures invests in every spinout), we have historically invested in 4-6 external companies per year. It's not a high number. The flip side of this is that we do invest, we're all-in.

What's your sweet spot(s) in terms of check size, valuation, and vertical?

We love to lead, we love to be early, and we love to be a part of building the company. When we invest, we're really invested (both with our dollars and our whole partnership's time). Our check size ranges from $500k to $3m, and we'll look at any company whose primary value proposition is based in technology (though we have a strong bias for software businesses). I in particular like to invest in obsessed founders running pre-launch B2B businesses, or post-launch B2C companies with signs from customers/users that they're really onto something.

What one portfolio company do you want to hype for us here?

Check out Joon Care! Josh Herst, Amy Mezulis, and the team are on an an important mission to treat depression and anxiety in teens and young adults. As many folks know, there is a mental health crisis in our country right now. Joon's product provides a new model for mental health care, combining one-on-one teletherapy sessions with a mobile app-based experience, with support and resources for parents. We had the privilege of co-founding the company in the PSL Studio with Josh and Amy and I'm personally inspired by their dedication to help ease this enormous problem felt by so many.

What do you think the next ten years looks like for Seattle/Pacific Northwest startups?

An increase in every trend we're already seeing — incredible talent not only spinning out of Big Tech™ companies, but also from the mini mafia's we've seen from Convoy, Rover, Zulily… not to mention all the second offices of Bay Area companies. I think the "Cloud City" thing is real and we'll continue to see a boom of great companies involved in internet plumbing. I also think software markets are even bigger than we all thought (which is so widely-believed now, it's a meme), and Seattle companies are great at bringing technology to legacy markets (real estate, lumber, immigration, healthcare, etc.). We're certainly going to keep doing that at PSL.

What song is currently getting the most run on your Spotify/Apple Music?

My top album of 2020 was Taylor Swift's folklore, so there's that.

Favorite shoes?

Nike Free Rn Flyknit 2018 Black/White

Favorite cooking ingredient?

Garlic

Anything else to say?

To founders: keep going. The early part of a compounding graph looks linear — and like a very low-slope linear at that. I'm a big believer that you should be as thrifty as possible in the early days and give an idea the time and breathing room it needs to develop customer love.

As an example, for the first 50 episodes or so of Acquired, growth looked modest and nobody ever talked about us. That didn't really change until 3-4 years in, and all of the slow-burning "goodwill" we had built up among listeners felt like it showed up all at once. Brands and trust take a long time to build.

Lastly, most businesses shouldn't raise venture capital and that is more than okay. If you have the possibility of a nice business on your hands, don't optimize for fundraising milestones… optimize for building the great business! Raise capital if you find yourself in a competitive situation, a winner-take-all-market, or you see a near-term opportunity for hyper-growth. It's harder to build a bootstrapped business early days, but it forces discipline you'll be glad you have no matter which path you choose.

Seattle VC Profile: Isaac Kato, Techstars

I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW

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Isaac Kato has had a heck of a career. From guiding two startups to exits as an entrepreneur, to stints at blue chip VC investment firms, to founding and raising >$200M for one of the world’s largest green data centers (in Iceland!), he’s never been satisfied to stay in his lane. And yet even with his impressive experience, Isaac brings humility, curiosity, and empathy to every discussion. So it figures he’s the perfect leader for Techstars Seattle, especially during a year like 2020. Our ecosystem is lucky to have Isaac as a mainstay, and I’m lucky to call him a friend and mentor.

What made you decide to be a professional investor?

I knew in college that I wanted to be an investor. At the time, most business oriented friends of mine were going into investment banking or consulting. I'd read "Barbarians at the Gate" (I know - terrible source of inspiration), and I decided I wanted to be a principal investor. I've hopefully been a more benevolent one than the raiders of the 80s.

What did you do before becoming an investor and how does that benefit your founders?

My first job out of college was, in fact, working for the Roy Disney family as a growth equity investor. But, since then, I've gone back and forth between being an investor and an entrepreneur (I've founded two companies and run three of them - two exited, and one is a growing, profitable company that I raised $200M for over ten years). I have little doubt that having walked in founders' heavy boots has given me a lot of useful experiences to share and definitely made me a more empathetic and effective investor. In my current role as MD of Techstars, which is a blend of investor and educator, having been on the investor side for a long while also improves my ability to help the Techstars Seattle companies raise capital and understand investor processes and psychology (and I've built up a terrific global network of early stage investors over the years).

What are your most successful investments so far?

I led the Series B at earliest revenue for Postini, which was one of the first application service providers (ASP = SaaS in the early 2000s). Postini was subsequently acquired by Google for $800M. I was among the earliest institutional investors in CCP Games, an Icelandic MMORPG company that was acquired by Pearl Abyss, a Korean games publisher for $425M.

Why should founders want you on their cap table?

1) I've got a ton of relevant experience, both as a successful investor and a successful founder, 2) I've got a huge network, and 3) I'm incredibly easy to work with and view my sole role as an investor as doing whatever I can to help increase my founders' chances of success. I've seen and worked with my fair share of mediocre (and sometimes just plain bad) investors, and I strive to be the diametric opposite of them.

How many new pitches (actual calls/zooms) do you take per month?

Techstars is a funny job, in that we take the normal early stage investing process, chop it up, and then repackage it in a non-traditional way, such that the vast majority of our recruiting/screening takes place during a concentrated few months. Last year, I took about 200 zooms over a five month period.

How many new investments do you make per year?

We pick ten companies per year for Techstars Seattle, and I make 3-4 angel investments per year personally.

What's your sweet spot(s) in terms of check size, valuation, and vertical?

Techstars Seattle will invest $120K per company, usually into pre-seed and seed stage companies across a wide range of tech verticals. I myself typically write $25K - $50K angel checks into pre-seed, seed, and the occasional Series A.

What one portfolio company do you want to hype for us here?

I love all my children, but you can see the awesome members of the 2021 Techstars Seattle cohort here: https://www.techstars.com/newsroom/2021-techstars-seattle-accelerator-companies. (Did someone say, "cop-out!?!" Ahem.)

What do you think the next ten years looks like for Seattle/Pacific Northwest startups?

My magic 8-ball says, "Outlook good!" I do worry about how frothy the market for tech funding in general has gotten, but then again I felt that way last year, and the year before, and the year before that, so… Regardless, in the long run, the increasing presence of big tech cos here can only be beneficial for the startup ecosystem. Sooner or later, a percentage of folks working at those places will inevitably get the startup itch, and once they take the dive, it's hard to go back. The flywheel is spinning.

What song is currently getting the most run on your Spotify/Apple Music?

Parklife, the 1994 Blur classic. I've also been wearing a lot of tracksuits recently. Sergio Tacchini 4ever.

Favorite shoes?

It's a tossup between my Dunlop insulated wellies (because my backyard is a wet, muddy mess), my ten-year old Sorel Manawan house slippers, and my Scarpa TX Comp Telemark ski boots. I haven't worn anything stylish on my feet since we went into lockdown. Kirby, forgive me for my sins...

Favorite cooking ingredient?

Does dry-aged ribeye count? I keep it simple with an Adobo rub.

Anything else to say?

In all seriousness, as a relative newcomer who has worked in the Bay Area, London, and Boston, one of the things I love about the Seattle/PNW tech ecosystem is how mutually supportive a community it is. I hope we can preserve that spirit for years to come - I certainly intend to do my part. Oh, and Kirby, I have some really nice bourbon arriving next week. We need to do that backyard hang.

Seattle VC Profile: Zane Khatib, Brighton Jones

When I started Ascend in 2019, I realized even though I was o-l-d OLD, I had more in common with the folks in town who were earlier in their professional investing journeys than the venerable VC’s I’d pitched as a founder. I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW

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Zane Khatib is the kind of person that makes me optimistic for the next phase of Seattle’s startup ecosystem growth. He’s energetic, positive, intelligent and curious. He handles everything from sourcing to LP relationships and fund admin, all with aplomb. Glad I’ll get to say I knew him when…

What made you decide to be a professional investor?

I grew up watching my mom found and grow two businesses. Seeing the passion and drive required to build something from the ground up became inspiring to me and ultimately, manifested in me wanting to spend my career working with startups. As I went through undergrad, I searched for ways to get involved in the Seattle VC ecosystem. Primarily done through persistent (and probably irritating) LinkedIn messages to entrepreneurs and investors to grab coffee or volunteering to support due diligence efforts at local angel investment groups. Every interaction with founders has been a rewarding and educating experience and continues to be so. Needless to say I have no plans to make a career change.

What are your most successful investments so far?

We have just finished deploying our first fund and have recently completed raising our second. We are still in the early years so this is difficult to answer now, but I look forward to having multiple answers to this question in the coming years.

Why should founders want you on their cap table?

The easy answer is that our group, Brighton Jones Investment Partners (BJIP), is comprised of exceptional LPs who bring a unique mix of expertise, operational acumen, financial aptitude, and business connections to the table. Tyler Mayfield and I only invest in founders that we believe in and plan to support fully in any way possible. This past year has been a challenging one for most startups and has really put us to the test. Rather than speak to this ourselves, we’d prefer anyone interested to simply reach out to the entrepreneurs we back.

How many new pitches (actual calls/zooms) do you take per month?

The deal flow has increased exponentially over the years. Hard to put a number to it, but we try and be as intentional as we can with our time and founders.

How many new investments do you make per year?

Target 6-8

What's your sweet spot(s) in terms of check size, valuation, and vertical?

Our sweet spot is between $1m-$2.5m. We have a broad mandate so our investments have spanned across various verticals from AgTech to consumer goods, however, we tend to steer clear of anything that will require FDA clearance (as fun as that process sounds). In terms of stage, this is vertical dependent, but we typically target seed – series A.

What one portfolio company do you want to hype for us here?

Beta Hatch. Awesome company led by an impressive founder/CEO, Virginia Emery. Excited to watch them grow!

What do you think the next ten years looks like for Seattle/Pacific Northwest startups?

The success of Seattle based startups like Convoy, Icertis, Highspot etc. is a testament to the brilliant minds that have flocked to Seattle over the years. With the continued success of so many young companies, we are going to continue to see remarkable new founders roll out and create something of their own. While COVID has changed the fundraising dynamic, I believe that the VCs that are local will be able to provide unique value to entrepreneurs as they navigate the challenging road of building a business. I look forward to supporting and participating in the growth that will occur within the PNW’s startup ecosystem over the next decade.

What song is currently getting the most run on your Spotify/Apple Music?

Ahh that’s tough to answer.. I am guilty of listening to a song nonstop for a couple days and then moving to the next. Right now the song of the day is either Chemicals by SG Lewis or Slipping Away by Leisure, but will likely be a completely different artist and genre by the end of the week.

Favorite shoes?

My white Nike Blazer Low LE or Adidas Ultraboost. Unfortunately, both get absolutely destroyed in the Seattle weather 😃

Favorite cooking ingredient?

Answering this implies I know how to cook. If I have to pick one I’ll go with Montreal Steak Seasoning.

Anything else to say?

Excited to be a part of this blog series. Looking forward to what the future holds for both Ascend and BJIP!

Seattle VC Profile: Rob Eldridge, Tapas Capital

When I started Ascend in 2019, I realized even though I was o-l-d OLD, I had more in common with the folks in town who were earlier in their professional investing journeys than the venerable VC’s I’d pitched as a founder. I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW

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Rob Eldridge was the CFO of Amazon’s China, Japan and India businesses. After that, he was the VP of Product for Fulfilled By Amazon (FBA). Now, he runs Tapas Capital, a burgeoning micro VC fund. There are few investors in Seattle with a more impressive operating track record. And yet, when I met him a few years ago, I was struck by how understated he was. Instead of a bombastic, “here’s how it oughtta be” grizzled vet, Rob brings curiosity and reserve to every relationship, allowing entrepreneurs to lay out their thoughts and giving space for the conversation to breathe.

What made you decide to be a professional investor?

I enjoy building and operating businesses and I realized how much I missed that after I left Amazon during my sabbatical/semi-retirement period. I was doing some early-stage founder advising and personal investing and thought I would marry the two activities and find a way to be more involved, and aligned, with a network of early-stage founders and their projects. That is when I decided to become a full-time VC.

What did you do before becoming an investor and how does that benefit your founders?

Product management, operational finance, investment banking, barkeep, housepainter, pedicab driver, English teacher. Had a lot of jobs, but technology has been a big part of it. At heart, I’m a tech geek – I learned to program in the early-80s and am now teaching myself python. In short, I have been involved in technology-related businesses since the early-90s and have built, operated and advised teams in a wide-variety of industries, on multiple continents, including most recently at Amazon where I spent a dozen years, and before that at Broadview, a boutique technology M&A firm based in Silicon Valley, and Sun Microsystems.

What are your most successful investments so far?

We’re early in our lifecycle and our portfolio companies are still growing and experimenting. I honestly feel like all of our companies have been pretty successful. It isn’t easy to build something from scratch, but products are being launched, teams are being built, customers are engaging, and feedback loops are operating. That seems like a good measure of success in the early days of a company’s evolution.

Why should founders want you on their cap table?

Between Greg and I, we bring decades of experience at Amazon.com (and elsewhere) where we built, operated, and scaled some of the world’s most innovative companies and we apply those learnings and our network to benefit founders in our portfolio.

How many new pitches (actual calls/zooms) do you take per month?

I see about 30 projects a month and take initial calls with about half of those project’s founders to learn more about them, what they are building, and determine if there is the potential for an investment fit.

How many new investments do you make per year?

Between 7-10.

What's your sweet spot(s) in terms of check size, valuation, and vertical?

Our average check size is about $100K and we prefer to invest early in a company’s lifecycle (pre-seed or seed rounds), although we have selectively made a couple later-stage investments. We are sector agnostic, and while we have invested in a handful of hardware companies, we get most excited about software-driven businesses creating brand new categories or operating in greenfield spaces.

What one portfolio company do you want to hype for us here?

Aaah…the Sophie’s Choice question. Laura Malcolm at Give InKind, Sarah Haggard at Tribute, Shane Kovalsky and Vince Coppola at Mystery, Ian Freed at Bamboo Learning, Kris Bleisner at Vega Cloud, Scott Hix at Avocor and Kevin Sun at Dex are all PNW-based founders working on some really cool products and we are lucky to have the chance to work with them.

What do you think the next ten years looks like for Seattle/Pacific Northwest startups?

I think the future is incredibly bright. The critical ingredient of highly qualified, entrepreneurial founders exists in abundance in the PNW and the supporting infrastructure of early-stage VCs, founder mentoring/networking forums, focused support for underappreciated founders, and an expectation of reinforcing success by giving back to the community are all being built and grown. We still have some progress to make along all of these dimensions, but I’m really excited to be part of such a vibrant and dynamic community.

What song is currently getting the most run on your Spotify/Apple Music?

Been revisiting Miseducation of Lauryn Hill quite a bit lately (which btw just reached Diamond status), as well as creating a list of inspired (e.g. as good as or better than the original) covers. Obvious ones like Johnny Cash’s version of Hurt, Alien Ant Farm’s Smooth Criminal, Red Hot Chili Peppers’ Higher Ground and Nancy and Ann Wilson’s Lincoln Center performance of Stairway to Heaven are all on my list. But would love to hear who/what else should be considered (@robeldridge).

Favorite shoes?

Nike sneakers or flipflops

Favorite cooking ingredient?

Russell Wilson 😊. Think we should let Russ Cook!

Anything else to say?

Thanks for the opportunity to be a part of this project. Go Huskies!

Seattle VC Profile: Minda Brusse, First Row Partners

When I started Ascend in 2019, I realized even though I was o-l-d OLD, I had more in common with the folks in town who were earlier in their professional investing journeys than the venerable VC’s I’d pitched as a founder. I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW

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I met Minda when both of us were still angel investing and exploring whether a “second career” in venture capital was something worth pursing. It turns out, for both of us, it was - and for many of the same reasons. I admire Minda’s founder-first perspective as well as the way she brings her whole self to the table. Whether raising millions of dollars to aid families in need during COVID, or raising her first venture fund, Minda’s infectious (pun intended) optimism rubs off on everyone around her, while her diligence and intellectual rigor bring the best kind of focus to her portfolio.

What made you decide to be a professional investor?

The leap came when I met Yoko Okano, my co-founder at First Row Partners a few years ago when we were in the angel group community as fund managers, investors and organizers.  We clicked as collaborators and co-investors.  We share and discuss divergent viewpoints really well, and our career goals align.  We didn’t take starting a firm lightly, either. We spoke to a lot of fund managers about the challenges of moving from angel investing to venture fund management.   Having our own firm gives us maximum flexibility and control for defining an investment strategy and deploying capital. I have a non-traditional background for venture capital, but one that I hope becomes more common.  

The opportunity to expand my scope and expand professionally, as a venture partner for 2048 Ventures, means I can lead pre-seed rounds (First Row doesn’t yet lead rounds.) It means deploying more capital to early stage companies and being strategically involved in their raise.  The 2048 ecosystem of founders and investing team offers more sounding boards and deal circulation outside of Seattle. And, they are excited about Seattle deals!

What did you do before becoming an investor and how does that benefit your founders?

I was a ‘lynchpin’ employee or co-founder at early stage startups for 20+ years, after five years doing systems integration projects for large product companies like Dial Corporation, Siemens, Motorola, HP and LSI Logic.  I was at Andersen Consulting, now Accenture.  I don’t code, but I’ve done every other role, in some part, at some point. I’ve worked across solutions in mobile apps, blockchain, affiliate marketing and lead generation, eProcurement SaaS + marketplace, and retail tech.  “Figuring things out” has always been part of the job. So, I’ve also become good at sharing what I’ve learned.

Founders have said they appreciate my clarifying questions rather than doing ‘advice giving.’  Having been in startups for over 20 years, I’ve seen a lot. But it isn’t the direct application of a specific experience that helps, usually.  I like to think I have a few good stories, though. Startups have a lot of ambiguity and the best way to navigate is by asking good questions and trying to connect dots.

These discussions begin at the earliest stages of meeting founders and really get going post-investment. In our initial meetings, founders frequently say things like, “Wow, you really get it.  It feels like you were in our launch planning meeting last week!”

What are your most successful investments so far?

One of the hardest things about investing in pre-seed startups is the long feedback cycle of 5-10 years.  I’m only a few years into investing, so I don’t have a ‘big exit’ story from an investment to share.  I am delighted to have led the investment in Xemelgo as the fund manager for Seattle Angel Conference.  They are creating the ‘digital twin’ of a factory floor with apps that pull sensor and other physical-layer data together.  Being able to see their internal development and external growth (during COVID!) has been rewarding. 

Why should founders want you on their cap table?

We call our firm “First Row Partners” because we see ourselves as being in  their 'first row' of supporters, and we respect that founders are the ones doing the hard work and bringing a big idea to life.  During the investment decision process, we identify the key milestones that the company needs to hit and which ones we can move the needle on.  It sets expectations on both sides and helps us scale our time with each company.  My goal is to use the founders’ time well because it’s a scarce resource.

How many new pitches (actual calls/zooms) do you take per month?

Maybe 30? It varies, and I am selective about meetings by asking for key information upfront. But I am all in on cold outreach by founders. I see a lot of pitch decks and wish every team in the PNW was on my radar.  I try only to take a founder’s time if there’s a true chance for an investment.  I have separate mentoring time on my calendar and find ways to be accessible through CoMotion at the UW and other accelerator programs. I miss our downtown Seattle coworking hubs like Create33, and I plan to organize some open/group coworking events once COVID safety permits. 

How many new investments do you make per year?

Unclear, but I hope to be part of 10++ investments between First Row and 2048.

What's your sweet spot(s) in terms of check size, valuation, and vertical?

Both 2048 Ventures and First Row like to meet teams early -- pre-accelerator, post-team formation. Typically, these teams have valuation caps below $5M. 

First Row checks are $25k today and will be $100-200k around 2021 Q2. We will be an early commitment in a round, but we don’t anticipate being the lead investor. 2048 Ventures is a high-conviction lead investor with an investment of $300-600k. At the pre-seed stage, that could be an entire round.

Both firms look for companies where technology or data is the differentiating factor. First Row emphasizes solutions where software is enriching our lives through community networks, at work and our consumer/retail lives. 2048 goes further -- adding deep tech, genomics, robotics and mobility.

What one portfolio company do you want to hype for us here?

I’m excited for Dathic, a company that 2048 and First Row co-invested in 2020 and I was the lead. They’re going to be the central source for modeling insights on the diverse Hispanic consumer.  Today, consumer packaged goods companies are accessing the Dathic model to pinpoint new and potential customers for their brands. The combination of the Dathic data sets and customer data is providing insights that already exceed what they thought possible.  

What do you think the next ten years looks like for Seattle/Pacific Northwest startups? 

I love this question!  I wrote a Twitter thread about it recently.  I think Seattle has a big decade ahead.  The trend I find compelling is that software developers are becoming creatives as software has a ‘supply chain’ aspect to it where APIs and dev tools enable developers to be problem solvers instead of coders. Given Seattle’s legacy of innovation and the strong arts economy, I’m hopeful that these  “tech creatives” and the creators in the arts community can see the similarities in producing big ideas and navigating ambiguity.  I’ve been fascinated by the connection between ‘creative destruction’ in both visual art and tech startups for a decade. 

What song is currently getting the most run on your Spotify/Apple Music?

I found a great trove of electronic ambient music this summer for star-gazing.  Magnetic Fluid by Aleksander Dimitrijevic is my favorite in that rotation. 

Favorite shoes?

My plum colored Ecco sneakers with a size zipper. 

Favorite cooking ingredient?

Butter!

Anything else to say?

We don’t require a warm intro. Founders can fill out a form on our website, and we will respond. 

If you want to keep tabs on First Row Partners, you can subscribe to our monthly newsletter here.  (There's a "bonus" art piece & discussion guide section in each issue.)

Ascend Venture Capital LP Profile: David Hersh, Founder, Jive Software #openlp

When I was a founder, I had no idea what a Limited Partner in a venture capital fund was. Now that I run my own fund, I want to bring transparency to founders and let them know where our money comes from. Our LP’s are an incredible group of individuals who often advise our founders and myself as we strive to create the next generation of world-changing startups (and funds!). -KW

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I met Dave when he was writing his upcoming book about getting startups “unstuck”. We clicked, I think because we both have experienced a version of the struggle to balance ourselves amid the pressures of growing a startup as a founder. Dave’s self awareness and humility are rare for someone with his outsized achievements. We’re fortunate to have him on board as an LP in Ascend, and happy he took the time to share his experience and insights here.

You're building a startup again at the earliest stages, after creating a $1B outcome with Jive Software. What drew you back into the game?

I tried venture and wasn't that great at it :). And a few years ago I discovered the art of the turnaround - acquiring "stuck" startups and turning them into strong companies. Mobilize was one of those….and I got hooked on it. I love the rush of startups, but as an older entrepreneur I get more energy from helping others now (employees, customers…the planet, where possible) than myself. It's like accessing a more powerful fuel source.

Taking off your founder hat, and donning the LP hat, what do you like most about early stage venture as an asset class?

The high beta. Tons of clear volatility but when it works, it can create phenomenal returns for everyone involved and hopefully a measurable change on society in its domain. It's also a lot more fascinating to learn about the investments - I don't spend nearly as much time looking at my fixed income funds :).

What's the best advice you have for a founder just starting out at the idea stage?

Don't fall in love with your idea such that you adhere to it too strongly. Separate your identity from the core concept (and the company itself) and let the market and team be the sandpaper and varnish that creates something magical. Become a steward for the company, not an iron fisted ruler.

You previously raised money from Silicon Valley giants like Sequoia and Kleiner Perkins. What's your best general advice to founders hoping to follow that path?

Like my answer above, the money, the VC firm and the partner you choose should all be in service of the business. Founders often see their startup as a series of funding rounds instead of optimizing the path to bring a new innovation to world. If the firm you're seeking is the best option to help take the company to the next level, and you work well with the partner there, great. But don't optimize for the name brand firm for ego reasons. It will come back to haunt you.

With Mobilize, you've spent a lot of time thinking about how people connect online. What do you think the next ten years look like for social networks?

There's certainly a pattern among younger generations wanting to use the new thing until it's no longer the new thing and then those product hang on to a laggard audience for awhile. If Discord gets acquired by Microsoft, watch how fast the teenagers find a new thing :). I think we'll see more of that continuing with new modes of fast, simple connections. With Mobilize we're focused more on professionals and enterprise buyers, so the trend that I see is more around data privacy and security, while at the same time embracing the best consumer experiences and new technologies like blockchain.

What song is currently getting the most run on your Spotify/Apple Music?

There's a lot of background work music being played….so I don't even know some of the artists that get the most play :). But I play the Westworld soundtrack a lot while writing. Run the Jewels for workouts / running.

Favorite shoes?

Brooks Glycerin for running.

Favorite cooking ingredient?

Italian sausage

Anything else?

I have a book called Fighting Shape (featuring Kirby!) coming out later this year, which is about getting startups unstuck. Stay tuned!

Seattle VC Profile: Yi-Jian Ngo, Alliance of Angels

When I started Ascend in 2019, I realized even though I was o-l-d OLD, I had more in common with the folks in town who were earlier in their professional investing journeys than the venerable VC’s I’d pitched as a founder. I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW

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Yi-Jian is not a traditional VC, but he seems to know about more deals happening than anyone in Seattle. His role running the Alliance of Angels, which deploys $10M annually into seed stage startups, is a handful. He works with entrepreneurs and angels in a highly coordinated dance of meet and greet, diligence and deployment.

What made you decide to be a professional investor?

After graduation, I was fortunate to join a company that offered a rotation program for new hires to try out different roles. One of those roles was a stint in their corporate venture capital group, and I had so much fun there that I decided to enter the business.

What did you do before becoming an investor and how does that benefit your founders?

I grew up in South East Asia, went to college in New Zealand, and spent some time in technical sales and business development. Over the years, I’ve had the opportunity to get to know a wide range of people, including the 140 investors in Alliance of Angels, the organization that I now run, as well as many other investors and founders in the Pacific Northwest. Always happy to make the right connections for entrepreneurs I meet.

What are your most successful investments so far?

Clarisonic, DocuSign and Elemental Technologies.

Why should founders want you on their cap table?

The organization I run, Alliance of Angels, has had the privilege to back more than 250 founders over the years, including the largest number of women-led startups in the Pacific Northwest. I endeavor to provide an efficient way for entrepreneurs to connect with 140 angels at one go, a group of folks who collectively represent a diverse range of entrepreneurial, industry vertical, and functional experiences.

How many new pitches (actual calls/zooms) do you take per month?

30

How many new investments do you make per year?

20

What's your sweet spot(s) in terms of check size, valuation, and vertical?

Typical check size $250k-$500k. Sector agnostic, stage agnostic, and focused only on startups headquartered in the Pacific Northwest.

What one portfolio company do you want to hype for us here?

SyncFloor, a marketplace for sync music. Awesome founder, large market opportunity, and also an Ascend portfolio company.

What song is currently getting the most run on your Spotify/Apple Music?

Kiss The Rain by Yiruma

Favorite shoes?

Bata

Favorite cooking ingredient?

Sambal

Seattle VC Profile: Geoff Harris, Flying Fish

When I started Ascend in 2019, I realized even though I was o-l-d OLD, I had more in common with the folks in town who were earlier in their professional investing journeys than the venerable VC’s I’d pitched as a founder. I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW

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Every time I talk to Geoff Harris I learn something. How best to work with founders, how to manage workflows, how to consider fundraising as an emerging VC - he’s incredibly generous with his experience and that most precious resource, his time. As a founding GP at Flying Fish, Geoff is changing the way SaaS- and AI-focused founders think about fundraising; increasingly, Flying Fish leads rounds that Valley firms would have scooped up in years past. We’re fortunate he shared more about his approach below.

What made you decide to be a professional investor?

The partners at Flying Fish were all angel investors in Seattle. We noticed that while angel checks were reasonably plentiful and a Series A was achievable if you could get to the right metrics, (Valley firms have traditionally entered the PNW market at Series A) companies had a really hard time raising a seed round from institutional investors locally. We felt this region deserved more seed capital and thus we started Flying Fish.

What did you do before becoming an investor and how does that benefit your founders?

Along with my partner, Frank Chang, I worked on speech and natural language at Microsoft. A core part of the thesis of Flying Fish is that machine learning and AI will fundamentally transform all industries. We look to invest in companies using ML/AI to competitive advantage. Companies started in 2021 have to have AI/ML at the core. Our background working at the forefront of these technologies gives us a unique perspective on what to look for and how to help our founders, whether that be recruiting talent, connecting them with advisors or signing up our former colleagues as customers.

What are your most successful investments so far?

We’re proud of helping achieve a great exit for AR company Streem which was a win for founders, investors and acquirer. That balance is not always easy to achieve.

Why should founders want you on their cap table?

First and foremost because we help get seed rounds done quickly. Our objective is to lead rounds and help founders syndicate so they can get back to building. Once we are working with a company we will do whatever is needed for that company. We don’t have a set playbook and are very responsive to the needs of the founders whether that be first customer connections, deep technical consulting, hiring or just a sounding board when things get rough. My partner, Heather Redman, has a particular skill in helping our founders find first customers in more obscure industries. Her network is beyond impressive.

How many new pitches (actual calls/zooms) do you take per month?

Highly variable, but it averages out to 50/month

How many new investments do you make per year?

Between 4-8

What's your sweet spot(s) in terms of check size, valuation, and vertical?

Our thesis is all around AI/ML. There are two types for us. One is platform AI/ML where the AI/ML is the business. Think of this as being tools that help practitioners build better models or broad developer APIs utilizing AI/ML techniques. The other is applied AI/ML which constitutes the bulk of our investments. Here our key question is whether the AI/ML is providing a competitive differentiation for the business – but the business could be in almost any vertical, per our notion that all industries will be disrupted by these technologies.

What one portfolio company do you want to hype for us here?

The parent in me would not want to recognize one companies achievements over another’s.

What do you think the next ten years looks like for Seattle/Pacific Northwest startups?

Nothing but bullish. We have the world’s greatest technology talent, great universities, high quality of life and a rational startup ecosystem. Things are very bright. We could use the Sonics back though.

What song is currently getting the most run on your Spotify/Apple Music?

If I’m honest – Taylor Swift - ‘tis the damn season. Mother Love Bone – Crown of Thorns is always a close second.

Favorite shoes?

Are we wearing shoes these days?

Favorite cooking ingredient?

Anything with a kick. Torchy’s sauce shipped up from Texas is a current fav.

Seattle VC Profile: Jacob Colker, Allen Institute for AI Incubator

When I started Ascend in 2019, I realized even though I was o-l-d OLD, I had more in common with the folks in town who were earlier in their professional investing journeys than the venerable VC’s I’d pitched as a founder. I admire and respect the new wave of Seattle/Pacific Northwest venture capitalists, and thought it would be fun to profile some of our region’s up and coming VC talents in these pages. —KW

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Five years ago, the late Paul Allen and Professor Oren Etzioni launched a commercialization arm of the Allen Institute for Artificial Intelligence. They gave Jacob Colker, Vu Ha, and Bryan Hale a blank slate and a one-line mandate: Build an incubator program to help the brightest minds in AI to start the next wave of world-changing technology companies. From a one-room office, Jacob and the team (shout outs to James Allard, Jen Dumas, Jackie Moe, and Brian Fling) have grown an unrivalled center of excellence for AI entrepreneurship. I had a front row seat for the evolution of the AI2 Incubator as a lucky advisor, learned a ton from Jacob along the way, and am really glad Jacob shared his story with Ascend here.

What made you decide to be a professional investor?

I spent many years as a founder and operator before a coffee with Chris DeVore helped me understand that venture investing was the perfect fit for me. But even if you are lucky enough to discover your true calling, few people will “just hand you” millions of dollars to invest. You have to build the case over many years, and work hard to earn the trust of LPs, and I’m fortunate that Dr. Oren Etzioni took a chance on me.

There are three reasons why I choose to be an investor:

1)    Founders are my kind of people They are crazy, driven, inspired, brilliant, and full of vision. And simply, I love being around these kinds of people. To me, there are few things more powerful than someone who is truly motivated to solve a problem with the hustle and drive of an “entrepreneurship-in-their-veins” founder. We are privileged to have such a wonderful community of entrepreneurs like this in the AI2 Incubator, with more joining every month.

2)    I truly love innovation — Artificial intelligence is powerful technology that is broadly applicable to numerous industries and fields. As a managing director at one of the world’s leading A.I. incubators, I get to learn about new business ideas and industries almost every week. These eclectic experiences offer an opportunity to see the world from a unique perspective, as many of these elements often map together in peculiar ways. This kind of continuous learning makes me come alive and it makes me better at advising our teams, as I can offer the best learnings/advice taken from a whole host of industries, business models, GTM strategies, technologies, and more.

3)    In my heart, I’m a teacher — If I didn’t have a career in entrepreneurship, I’d be a teacher. But it turns out that being an investor is the best of both worlds. Before I joined the Allen Institute for Artificial Intelligence, I was fortunate to spend six years teaching entrepreneurship in the MBA program at the University of Washington Foster Business School. During that time, I had hundreds of MBA students come through my classes and I loved every minute of it. It turns out that being an investor and board member is not that different from being a professor: You roll up your sleeves everyday and do your best to offer sage advice, be a sounding board, help solve problems, and guide the professional development of people who have put their trust in you. And of course, when one person teaches, two people learn. So I get to feed my own algorithm everyday and get smarter/better at my job with each conversation.

What did you do before becoming an investor and how does that benefit your founders?

I’m a founder myself—with expertise in marketing/GTM, sales, partnerships, business model design, and fundraising strategy. I’ve typically been the person that pairs with a technical founder to take a novel technology to market.

Previous to my work at the Allen Institute for Artificial Intelligence (AI2), I wore every non-technical hat in a startup (CEO, CMO, GM, Founder). I started collaborating with technical minds using data mining in 2006, crowdsourcing in 2008, and machine learning in 2011. And at AI2, I get to partner with the researchers here that are pushing the boundaries of computer vision, speech, NLP, and deep learning.

But more than anything else, I get it, and I’ve likely been there before. There’s an old saying that “healthcare professionals marry healthcare professionals” because they’re the only ones who really get it. A spouse who also works in healthcare gets it won’t hold it against you for cancelling dinner plans at the last minute, because you had a patient crashing and couldn’t leave. Other doctors or nurses understand what you’re going through. I think the same is true for entrepreneurship.

●      I know what it's like to quit your job (or work endless nights/weekends) and bet your financial well-being and personal reputation on the product vision in your head. And yes, it’s normal to wonder if that vision is really a hallucination.

●      I know what it's like to jump on that red eye flight to New York to go close that customer with a last minute in-person push, because that’s what it takes to get the job done that week. 

●      I know what it's like to be three weeks from an empty bank account, worrying if you’re going to make payroll, because several of your employees have mortgages and kids.

●      I know what it's like to do 16 versions of a pitch deck, only to toss it out and start all over again.

●      I know what it’s like to be told “no” by 24 VCs. Or have cofounders leave at the worst moments. Or to get threatened with a lawsuit. Or have your brilliant go-to-market plan not work out after weeks of planning and research.

●      I also know the incredible feeling that comes from finally finding product market fit. Or when your bank account stops decreasing from monthly burn and starts increasing from revenue. Or looking out across the many desks in your office and realizing just how many jobs you’ve helped to create. And, I know what it’s like to finally see a company that you’ve spent years helping to build—exit for many millions of dollars.

I’ve been there. I get it. And I can help you work through it.

Why should founders want you on their cap table?

I do all of my investment work alongside our extraordinary team at the Allen Institute for Artificial Intelligence, and the entrepreneurs or startups that take investment from us are able to tap into six truly unfair advantages. 

1)    A.I. research expertise — Google has DeepMind, Facebook has FAIR, and Microsoft has MSR-AI. But these A.I. research groups are designed for the benefit of these big companies—not fledgling young startups. The AI2 Incubator is part of the Allen Institute for Artificial Intelligence, with over 175+ A.I. PhDs, researchers, engineers, and support staff. Our institute is one of the only places in the world where early-stage startups or entrepreneurs can get mentorship from the same caliber of A.I. talent employed by giant tech companies.

2)    Applied A.I. expertise — There are now 20,000+ new A.I. papers published annually on Arxiv.org. But there’s a big difference between being able to read a research paper and being able to practically integrate that research into a new product. Our teammates at AI2 have collectively built many dozens of AI-first products and have tremendous expertise with the pitfalls and challenges of doing applied A.I. the right way.

3)    Recruiting pipeline (A.I., engineering, and business) — We guarantee that you will meet at least one cofounder or first hire through AI2. In fact, in the last 18 months, 75% of all our startups’ founders or first hires were a direct result of the AI2 network, with 100% of teams successfully finding a teammate here. We can deliver these results because over 11,000+ people apply to jobs at AI2 each year and many tens of thousands more spend time on our career page, LinkedIn job post network, come through our word-of-mouth network, and more. We are exceptionally good at helping to place top A.I. talent on teams and are equally capable of finding experienced business entrepreneurs to match with A.I. founders.

4)    Pre-seed expertise — We live at “whiteboard early,” and over the last five years, we’ve helped dozens of founders to go from the whiteboard to a successful multimillion dollar venture funding round… again, and again, and again. In fact, two thirds (66%) of entrepreneurs that formally join our incubator end up raising a multimillion dollar seed round.

5)    Community — Building a company is hard, but it’s a lot easier when you have a “village” of people surrounding you as cheerleaders, thought partners, drinking buddies, BFFs, and network amplifiers. That’s what happens when founders join our incubator. Almost overnight, entrepreneurs get access to a vibrant and intimate community of people who want them to succeed. It's “fellowship” at its very best.

6)    Paul Allen network — The Pacific Northwest continues to benefit from Paul Allen’s incredible legacy and many years of contributions to our community, that extend well beyond being the cofounder of Microsoft. The Allen Institute for A.I. is part of Paul Allen’s Vulcan: A vast network of organizations that includes the Seattle Seahawks, Portland Trailblazers, Allen Institute for Brain Science, Allen Institute for Cell Science, Allen Institute for Immunology, Vulcan Capital, Vulcan Real Estate, the MoPOP Museum, the Allen School for Computer Science and Engineering at the University of Washington, and more. Our “part of the family” relationship with these amazing organizations has helped our entrepreneurs to get introductions to customer discovery contacts, facilitated learning opportunities, potential pilot customers, and more.

How many new pitches (actual calls/zooms) do you take per month?

I took 249 first coffees in 2020—or about five per week. (Thanks to Calendly for the data!)

How many new investments do you make per year? What's your sweet spot(s) in terms of check size, valuation, and vertical?

We are an AI-first, pre-seed incubator, so everything we do falls into that thesis. We do 10-20 pre-seed investments each year, ranging from $100,000-$900,000. These range from individual entrepreneurs who need a year to figure out a new startup, or a pre-seed company starting to gain some early traction.

What do you think the next ten years looks like for Seattle/Pacific Northwest startups?

Oren Etzioni and I wrote an article in October of 2019 that we still believe holds much truth. Despite the pandemic, I remain incredibly bullish on what we are going to accomplish together as a region. I’m “all in” on Seattle.

What song is currently getting the most run on your Spotify/Apple Music?

I’m obviously biased ;-) but shameless self promotion… Recently, my old songwriting partner (Nick King) and I launched a new music project called “King//Colker” as a fun creative outlet during the pandemic. Our first single 'Not Alone' just hit 500,000+ plays on YouTube. Apparently, we’re “huge” in Mexico City. 😂

Favorite shoes?

Snorkel fins.

Favorite cooking ingredient?

Mazi 401.