Navigating Early-Stage Investment: Insights and Strategies from Aditya Naganath, Principal Investor at Kleiner Perkins

Aditya Naganath’s venture capital philosophy is straightforward: “If you build it, they will come.”

As Principal Investor at Kleiner Perkins, Naganath has built quite the resume for himself, including a blend of operational roles at major tech companies and expertise in business strategy. 

Naganath’s professional journey is marked by his hands-on engineering positions. Post-graduation, he served as technical lead at Palantir, where he played a role in developing the software giant’s Foundry Platform. He went on to earn an MBA from Stanford’s GSB and took on the position of product manager at Google, overseeing tools that helped SMBs during the pandemic.

Joining Kleiner full-time in 2022, Naganath is now part of the firm’s elite team of investors. His focus is on early-stage enterprise software, including application infrastructure, security, and AI. 

Naganath was a recent guest at Ascend’s AMA, a monthly session for portfolio founders where we bring in experts on relevant topics (this month's focus: getting to Series A). He shared insights on fundraising strategies, crafting compelling narratives, and advice for out-of-geo startups. Keep reading for our main takeaways from that conversation.

“You need to be able to zoom in and out of your business:” Founders should strive to deeply understand their market and parlay that understanding into compelling storytelling as well as sound justification of their approach. The best ones often combine this with an obsession about the details of their product and their company's operations and finances. 

Product craft: Founders should be obsessed with product craftsmanship. “It’s about the details and having a taste for the product,” he said. He sees this as a crucial factor in successful investments like Rippling, Figma, and Loom.

Not all metrics are created equal: Revenue, while important, should not be the sole indicator of potential. Naganath recommends focusing on “atomic units of value” rather than data like NRR, ARR, or burn rate. He points out that measures like net new ARR better indicate growth pace. For instance, infrastructure companies face delayed monetization, and it’s up to investors to understand these trajectories. 

Naganath’s three tips for raising your Series A: 

  1. Avoid making hasty decisions and accepting initial offers without consideration. “Think about your cap table construction,” he said. 

  2. Do not raise too early just to get more dollars into your company. This can turn away quality investors. “I’m not saying to wait until you have three months of runway left,” he said. “But the risk you run is that a good investor might say, ‘Hey, I don’t think you’re quite ready.” 

  3. Be authentic and transparent about why you are fundraising and the current situation that your startup is encountering. “The investors who shy away from that will probably not be a good fit anyway,” he said. 

Effective investor engagement: Be transparent about the framing of your outreach and meetings with investors, whether that’s a formal pitch meeting or relationship building. In the latter case, it creates the option of building a relationship with the investor at a more authentic level, and avoids pushing the investor to make an immediate investment decision. It’s also wise to be considerate of your own time to avoid spending too much time on relationship building, rather than working on your startup, which can appear as a negative signal to investors. 

Navigating VC pitches for founders outside major tech hubs: The challenge for founders outside major tech hubs, like the Bay Area and New York, is proving you can attract top talent, especially in fields like AI. “You have to make the case for your talent pool,” Naganath said. 

Investors may have biases about talent from big companies like Microsoft and Amazon, assuming they lack startup DNA. He adds, “On the flip side of this is that there are certain values. Founders who are too plugged in for their own good just come across as bravado, arrogance or immaturity.” 

Parting thoughts: Founders should continually refresh their perspective to deeply understand the market they are venturing into and commit to their craft. 

“Good things will follow,” he said. 

Best Practices for Requesting Warm Intros From Your Investors

Your investors hold extensive networks that can be invaluable for warm introductions to potential customers, advisors, and candidates. Making this process seamless for your investor is key. Here's a straightforward guide to assist you.

1. Identify Your Targets on LinkedIn:

  • Ensure you are connected to your investor

  • Click on their "connections" list 

  • Use the "All Filters" tab to refine your search. Free text in the Keywords section "Title" and "Company" can be most helpful. (Pro-tip: LinkedIn Sales Navigator offers a free trial and has much more robust search filters available.)

2. Create a Target List:

  • Compile a concise list of no more than 20 targets connected to your investor. 

  • Include the target's name, title, company, and LinkedIn profile

  • Send to your investor and ask them to identify which folks they feel comfortable reaching out to

(example)

3. Prepare the Forwardable Emails

  • Once your investor identifies which targets they can reach out to, craft individual forwardable emails

  • Ensure the emails are easy for your investor to forward with a personal note

(example)

Pro-Tips for a Great Forwardable

  • Include a link to the target's LinkedIn profile so your investor can quickly orient

  • Add specific language to show you've done your research on this person (the above example notes the target's past work experience)

  • Keep it short and to the point

  • Make a clear ask (ex. "Would you be open to a call to discuss?")

  • Add additional supporting info about your company below your signature line

Seattle VC Profile: Matt Wang

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

Matt Wang is the New Ventures Lead at Pioneer Square Labs, a startup studio and early-stage VC fund in Seattle.

What made you decide to be a professional investor?

Like 90% of people in venture, I didn’t have a super linear path into investing. Before my current role, I was a consultant with BCG, but knew that I wanted to pursue a career in technology investing afterwards because I dabbled in growth equity investing in college. There were a few different potential paths I could take, so I reached out to Greg Gottesman at PSL to see if he had any thoughts on what might be the most interesting, and it just so happened that Greg was thinking about hiring a Chief of Staff at the time. We got along super well after taking a walk in Pioneer Park on Mercer Island, and I was signed up with PSL within the next week. 

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

It’s not the most fashionable thing in this industry, but I had been a consultant at two different firms: BCG, and before that, Innosight, which is Clayton Chirstensen’s firm. I also spent a year between the two working on incubation and new verticals at DoorDash’s NYC office. Seeing the breadth of problems that incumbents and scaling companies faced in those roles gave me a ton of perspective - not only into the functional challenges of managing and growing a business, but also on the many different ways that companies build their strategy (deliberately or not). Having those experiences to draw on has helped me work with our founders on a wide breadth of issues, like helping our climate-focused spinout ever.green understand the layered incentives of a potential enterprise customer, or thinking through how a credit hedge fund analyst might engage with LoansIntel, which is a debt intelligence platform that we invested in. 

Why should founders want you on their cap table?

It’s simple - PSL is a firm of operators and investors. As a studio, we build businesses from scratch, which gives us an intimate understanding of the challenges of starting companies, and as a venture firm, we’ve collectively seen and helped with multiple industry-defining companies. I personally work across both sides of our business, and will also lead studio projects as the on-point person to execute on creating a company out of an idea (which often results in killing it too!) Our network, experiences, and operating strength equip us to know how we can provide the most leverage to the founders we work with, and also gives us a good idea of when to help vs. when to get out of the way. 

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

I have a unique role working both across the PSL Studio and Fund, so I mainly take inbound pitches in industries that I’m excited about. I would say that I take around 20 new meetings a month. 

How many new investments do you make per year?

Our fund invests in 4 - 5 new deals per year, and our studio aims to spin out 4 - 5 new companies per year. 

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

While we invest across Formation, Seed, and Series A stages, Formation is our sweet spot. 70% of our first checks are within 60 days of incorporation. We prefer to lead, and initial check sizes range from $1-3M. 

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

I love companies that disrupt entrenched industries and try to make the world a better place to live in, and especially love companies and teams that have a good story for why they are the ones to do it. Last year, we spun out a company called Felix and Fido that provides end-to-end veterinary services through both a clinic and through mobile services. The veterinary care space was at a bit of a breaking point - coming off of the pandemic, there was an explosion in pet ownership, and the increased demand collided with the decreasing number of veterinarians in the US (who have a job that is remarkably demanding and stressful). We thought we could build a company that treats customers better while also providing veterinarians with the work environment that they deserve, and we were incredibly fortunate to find that Gavin Woody, now the founder of Felix and Fido (as well as a record-breaking ultra athlete, former airborne ranger, and whose parents both had careers in veterinary medicine), agreed with us. It was exciting to watch an idea go from a whiteboard to a clinic opening party. 

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

PSL was founded on a geographical thesis: we believe that Seattle is one of the nation’s greatest sources of startup talent on account of the exceptional companies and universities in the area. The PNW hosts the centers of cloud computing, logistics, ecommerce, and enterprise software, and I believe that success begets success. With the recent excitement in generative AI, and the incredible community of builders that we’re lucky to have here, I think that the next generational tech company will be founded (or perhaps has already been founded) in Seattle. 

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

Geoff Entress showed me Keith Jarrett’s Koln Concert. It helps me focus! 

Favorite shoes?

Whatever is closest to the door on my way out. Right now it’s a pair of goretex Nike sneakers. This was after catching a lot of flack for wearing a pair of dusty Alden loafers during our summer party. 

Favorite cooking ingredient?

Paprika! Also have you ever noticed how much soy and corn is in everything we eat? My fiance is allergic to both. Try avoiding them for a week.

FOUNDERS BASH 2023 - SEATTLE STARTUP PHOTO GALLERY

More than 1100 founders and investors registered for Founders Bash 2023, what a night. Shouts to our partners at AWS Startups, Stifel Venture Banking, Summit Trail Advisors, WSGR, Reverb, and Mary’s Place and Special Olympics of Washington!

Seattle VC Profile: Colin Tobias

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

Colin Tobias is a Partner at Semper Virens, investing in technology transforming work, health, and financial wellness.

What made you decide to be a professional investor?

My path into venture was non-linear, but I have always been interested in  technology, finance and investing so, in retrospect, it seems natural that I have ended up as a venture investor. I didn’t intentionally plan on working in VC, however as the opportunity arose I loved the idea of combining my interests and working alongside incredible entrepreneurs as they build enduring, impactful businesses! I was lucky enough to start my investing career at a growth-stage fund called Tenaya Capital learning under some amazing investors / mentors and now feel lucky to be a part of the awesome team at SemperVirens.

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

I started my career at a large finance and accounting firm in the Bay Area serving venture-backed startups as well as their investors (VC funds). I worked there for three years, during which I spent time across their valuation, audit and tax teams. That experience was a valuable foundation for how I think about and help our portfolio companies today as much of the financial engineering and corporate strategy is typically overlooked until it is too late. This experience is a great compliment to the benefit that our fund and ecosystem offers, which is focused on accelerating a company’s GTM (more on that below).

Why should founders want you on their cap table?

At SemperVirens, we have a very focused, thesis-driven investment strategy – investing in workforce, healthcare and financial companies that primarily sell B2B. We have built a strategic people-focused ecosystem that supercharges our portfolio by unlocking thousands of customer introductions and channel partnerships across 100+ CHROs of publicly traded companies like UPS, Visa, and Disney, as well as key systems partners, insurance carriers / payers , hospital systems, and brokers. It’s easier to show rather than tell, so view our awesome ecosystem here.

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

As a team, we’re lucky to meet with between 100-125 entrepreneurs each month.

How many new investments do you make per year?

We make 8-12 new investments each year out of our core Seed / Series A fund, as well as 3-4 growth deals out of our later-stage fund.

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

We typically invest in Seed and Series A companies with an initial check size between $500k - $5 million depending on round dynamics (stage, valuation, etc.).  We invest across three core verticals:

  • Workforce - essential solutions and services that are redefining the way employers and employees work.

  • Healthcare - technology-enabled healthcare products that help employers, payers and providers offer better care, reduce costs, and comply with new regulations.

  • Financial - software products that are used by businesses and consumers to enable, enhance, and disrupt financial services.

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

I’d be remiss not to mention our sole PNW investment, Karat. Karat created the Interviewing Cloud to conduct technical interviews on behalf of organizations hiring software engineers. Mo and Jeff are incredible founders and we’re lucky to be partners with them along this incredible journey.

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

While I am relatively new to the PNW, I am extremely bullish on the ecosystem - there is incredible energy and excitement as entrepreneurs are building the next wave of category-defining businesses supported by some great investors like Kirby and Jen. While my fund is based in the Bay Area, my goal is to make the PNW the second largest investment geography outside of Northern California!

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

I’m a big fan of the Spotify personalized playlists which tend to surface a lot of EDM / house music. That said, we’ve recently bought a record player which has reawakened my love for the classics – Led Zeppelin and Fleetwood Mac have been the staples.

Favorite shoes?

I am typically always seen in my Nike Killshot 2’s which are my daily wear - so much so that I have back-up pairs (my wife has been successful in getting me to branch out though!).

Favorite cooking ingredient?

Onions - such a staple to many incredible dishes and the smell of sauteed onions is always a sign that an incredible meal is around the corner.

Seattle VC Profile: James Wu, First Round

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

I was fortunate enough to meet James Wu when he had the idea for his first startup, and we invested shortly thereafter. James has a high EQ and is intellectually honest, a combo that makes him a great bet to become a steallar VC at First Round now that he has switched sides of the table.

What made you decide to be a professional investor?

Early on in my career, I cofounded AdaptiLab to help companies grow their machine learning and data science teams from hiring to productivity. As a technical CEO, I was able to empathize with the pain points of our customers, who were Heads of Machine Learning, and understand the unique challenges they faced. At the same time, I had to learn many key elements of company building, such as founder-led sales, team-building, and fundraising – all while iterating on a complex product and staying aware of the newest machine learning trends and innovations. Through this experience, I felt there was a growing opportunity for more specialized investors to support technical founders building their companies from zero-to-one.

When the opportunity to be First Round’s dedicated AI/ML & Infrastructure Investor came up, I was excited to leverage my unique skill set and experiences as a founder, operator, and researcher to help the next generation of technical founders. I understand the value of having investors who can assist with hard problems like sharing feedback on early prototypes, providing guidance on growing a developer community, architecting a complex machine learning system, sharing context around shifting trends in open-source software, making introductions to elusive MLE or DevOps candidates, and more.

In my current role at First Round, I focus on partnering with founders building AI/ML, Data, Devtools, and Security companies at the earliest stages of their company’s journeys.

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

From conducting ML and data privacy research in academia, to rolling up my sleeves and building a startup from founding to acquisition, to leading new machine learning projects at a fast-growing unicorn, I’ve experienced first hand the pains of building a startup and growing into the role of CEO as a technical founder.

After a research stint in academia, I cofounded AdaptiLab as a technical cofounder with one of my best friends to help companies scale their machine learning and data science teams. Being first-time founders, we had to quickly learn how to conduct customer discovery interviews, iterate on product feedback, figure out pricing and enterprise business models, fundraise from VCs and angels, and many more exciting elements of company building. We raised a seed round and signed Fortune1000s and Unicorns as customers. After AdaptiLab was acquired, I joined Amperity, a unicorn startup building an enterprise customer data platform, where I led new applied machine learning projects and contributed to patents and research papers on their core machine learning and data systems. 

All of these experiences have prepared me to become a partner that founders, especially technical ones, can rely on. Throughout a founder’s journey, they will encounter questions or challenges that their backgrounds will not have prepared them for. I hope to be the investor they turn to when they need additional context or a collaborative working session to figure out the right strategy to move forward. Whether it’s figuring out how to incorporate machine learning into your product, understanding best practices for hiring and leading teams, or learning how to conduct customer discovery calls and sell your product as a technical founder, I’ve gone through many of the same experiences, and can empathize with the same thorny problems.

Why should founders want you on their cap table?

First Round is focused on being the world’s best partner for founders at the very first stages of company creation. When founders work with us, they get investment team members (including me!) working side-by-side with them on their business' challenges. 

On top of that, our Operating Team is ready to support founders through the toughest parts of company building. Whether it’s our Pitch Assist Team crafting a Series A deck, our GTM Team finding prospective customers through Discovery Assist or our Talent Team connecting them to top-tier candidates, we're here to help across all their needs!

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

While First Round is a generalist firm (our portfolio), we have a number of distinct practice areas. I personally focus my investing on AI/ML & Infrastructure. This means I spend most of my time with AI/ML, dev tools, data infrastructure, and security founders. I'm also very interested in applications of ML to specific verticals or business problems, recently healthcare and life sciences.

Typical check size ranges from $1.5M to $4M, but we’ve gone higher and lower in some cases. Currently, our average initial investment is around $3 million.

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

Rewind.ai! Rewind is building the search engine for your life that enables you to find anything you’ve seen, said, or heard. It creates a searchable recording of what happened when, who said what during that Zoom meeting and every instance someone has ever brought up expense reporting hacks. You can try out their product now for free. Cofounded by Dan Siroker and Brett Bejcek.

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

I'm very excited for the future of Seattle's startup ecosystem. So many talented founders have been locked up at Amazon and Microsoft for the last decade, and I think the recent economic downturn combined with the wave of advancements in AI/ML has spurred many more founders to take the leap on starting a company. As a Bellevue native who built my startup primarily in Seattle, I'm looking forward to supporting the next wave of infrastructure companies being built in the region.

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

I don't really listen to much music but love podcasts. I've listened to every podcast from Acquired.fm and The Logan Bartlett Show. They're the best prepped podcasts telling interesting founder stories and startup journeys.

Favorite shoes?

Adidas Ultraboosts 1.0-3.0

Favorite cooking ingredient?

I could eat eggs for breakfast, lunch, and dinner and I have go-to dishes I'd cook for each.

Seattle VC Profile: Katelyn Donnelly, Avalanche Venture 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

katelyn donnelly.jpg

Katelyn Donnelly is a terrific investor. Whenever I partner with her for diligence on a new opportunity, or to think through how to help a mutual portfolio company, I come away impressed with her clarity of thought and her intellectual honesty.

What made you decide to be a professional investor?

I’ve always been an investor. Even in high school, I invested in public equities and thought about building a portfolio. I wrote my senior thesis on time zone arbitrage trading strategies. Investing is the greatest strategic game on the planet. I started Avalanche VC because there are some trends that are obviously the future and I wanted to make bets behind those that I had a competitive advantage or unique insight. It’s a privilege to be able to work with talented founders at the earliest stages.

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

I started my career at McKinsey and then founded the corporate venture arm of Pearson in 2012. I’ve been an investor for a long time and have a deep background in education - spanning early childhood to life long learning. I’ve also started a company (Delivery Associates) that was boot strapped, profitable, and still growing strong.

For founders, I bring a well-rounded background. I know what it’s like to be a builder, a capital allocator, and a market thinker. I can particularly help those in education because I have participated and published on those markets develop globally for over 10 years. On future of work, I’ve founded and scaled a global, remote-first company to over 100 FTEs so I intuitively understand the customer experience through first-person experience.

What are your most successful investments so far?

From my Pearson days, my most successful investments are chains of low cost, high quality school in emerging markets. Spark Schools and APEC Schools are the two big ones that I was the first significant lead investor in.

From the last couple years, a carbon negative hydrogen power company called Wabash Valley Resources.

My Avalanche investments are too early to tell.

Why should founders want you on their cap table?

I aim to be the best value per dollar. I’m honest, direct, straightforward, and always act in your best interest. I’ll bring the full force of my creativity, problem-solving, and network to every conversation.

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

100

How many new investments do you make per year?

20+ this year

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

Right now I’m doing $300K, pre-seed/seed, Future of Work/EdTech/Enterprise SaaS

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

I can’t pick favorites :)

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

Everything Maggie Rogers

Favorite shoes?

These No Bull Trainers get the most use these days!

Favorite cooking ingredient?

Everything I eat has olive oil in it.

Seattle VC Profile: Dennis Joyce, Tacoma Venture Fund

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

dennis joyce.jpg

Dennis Joyce is one of the most empathetic, supportive investors a founder can have on the cap table. He’s been dedicated to backing underestimated founders since before it was cool. Dennis is now a partner with emerging managers Tacoma Venture Fund, and shares his story below.

What made you decide to be a professional investor?

I was meant to be a VC. I just never knew it.

When I was younger, I never really had a clear career path that I was looking to pursue. I did pretty well in school but not great. I was ok in sports and music and other activities but did not distinguish myself in any particular field. I was a bit of a dabbler, who could pick something up quickly but never enough to gain mastery. I was mediocre at everything.

I always liked watching sports, then movies, and music, and later business. I always had a favorite athlete (Wayne Gretzky) or actor (Eddie Murphy) or band (Megadeth) that I was “invested” in.

In the late 90s, the first wave of celebrity VCs emerged, I was fascinated by these guys who made seemingly gobs of money investing early in companies like Netscape or AOL. I would read a story about Jim Clark investing in Marc Andreesen and making millions being the person to discover Netscape. It seemed so cool to me.

I had always been entrepreneurial and innovative. I’d start a band or business here or hatch an idea but I never really had the passion to make something my work. It’s as if I wanted to see something happen, but I never really had the passion to do it myself.

Over the years it dawned on me VC was perfect for me. It allowed me to support entrepreneurs, it allowed me to dabble in dozens of ideas without having to “pick a lane”. It allowed me to passionately support multiple endeavors at a time and dream of a better world. I get to support other people pursuing their unique passions

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

I’ve spent a little time doing pretty much anything you’d imagine. I grew up in a family business where my father managed real estate during the day while working as a security guard at night. I’m from a family of 7 and everyone took turns working at the family business. My childhood jobs were rolling coins (arcade money), painting apartments, renting apartments and stores, landscaping, and doing pretty much anything a small apartment complex.

After college I did some entrepreneurial things like a 90s version of Barstool Sports, spent a minute on Wall Street, and more time in real estate. I caught a break in business school, working at a VC firm in Japan, which is where I solidified my dream to work as a full time VC. Unfortunately, I had to take the long way around as I could not land a job after graduation. So I started back in real estate, did some rehabs and development. I later, invested in a couple entertainment products before finally returning to early stage investing – this time as an angel.

I began spending all of my time at the angel groups with the dream of one day being a real live, honest to goodness VC. After a few years volunteering my time at the angel groups I was able to connect with the guys starting Tacoma Venture Fund and we put a plan in place to start TVF. And here we are.

My career has had a million twists and turns and dead-ends before landing me at TVF. I think or all of the false-starts and frustration and realize they were all leading me to where I am now which is my dream job. In order to be successful you need the passion and commitment to make the necessary sacrifices it takes to be successful. If you are incapable or unwilling to make those sacrifices, you will not have success. You got to love it. I’ve never loved anything enough to make those sacrifices other than VC

What are your most successful investments so far?

The most successful ones are the one still operating. I am grateful to have about 20 still going strong and growing. I’ve done a few deals where I was in early that have had subsequent Series Seed or Series A raises, but I am still really early in my career and I’m still waiting for the “big one”. I am a proud investor of some great emerging companies such as Blokable, Ripl, Give InKind, Flavorcloud, Heroclip, Tribl, WeSolv, geeRemit, Cone and Steiner, and TVF’s newest investment Brightly.eco.

But no success feels as good as the disappointments feel bad. I’ll never get over the failures. It’s like losing a child.

Why should founders want you on their cap table?

Because I will have their back through thick or thin. They can text me 24 hours a day 7 days a week 365 days out of the year with good news, bad news, frustration, happiness and sadness and I will support them with every fiber of my being.

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

Probably 30-40 if I’m counting a demo day or an angel group screening session. I hear anecdotes of VCs seeing more than that but I wouldn’t be able to be attentive to many more than that.

How many new investments do you make per year?

TVF will do between 6-12 this year including follow-ons. We are just getting going so it’s hard to say.

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

First institutional raise until about Series A. Check size ranges from $150K – $500K although we may allocate more for a follow-on with high conviction. We are sector agnostic and we like to get decent economics on the deal so we can have some upside. Nothing fancy.

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

If forced to pick, I’ll say our newest one – Brightly.eco. It is a platform for conscious consumers.

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

The next 10 years will be a very busy time for the PacNW ecosystem. We’ll see a lot of startups emerge with great prospects and really experienced teams. I’m optimistic that we will continue to lead the country in stimulating innovation at the early stages. Hopefully we are just getting warmed up.

I’d like to see the emergence of a few more great VC firms and emerging managers build big funds such as Ascend.vc and us at TVF so we can lead big rounds on the founders that we love. In order to do that we must attract more capital to our funds from outside of the ecosystem. There is more than just three funds in Seattle and there are a number of great investors at the earliest stages. In 10 years, I hope TVF will be on our $150M Fund III.

I’d like to see some of the cliquie-ness I see disappear and for more underserved founders get the opportunity to raise big rounds from the big firms. I’d like to see more large risks being taken on people that would not normally get a shot (female founders and minority led teams). I’d like to see more capital deployed in secondary cities like Portland and Tacoma.

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

I’ve been preparing for years to answer a question like this so I can come off as cool and hip, and in the know. Since everything, even my music choices, is an investment, I need come up with a banger.

SZA – Good Days

I’ve been obsessed with SZA since the CTRL album. She’s a transcendent talent and you can’t fake talent.

Favorite shoes?

I never had cool shoes. I grew up playing hockey so no one really had cool shoes. Back in the day though I liked those Bo Jackson Nikes? Have they re-issued those?

Favorite cooking ingredient?

I put a little bit of Salt and Pepper in everything I cook.

Anything else to say?

To me everything is an investment. In life we invest our time, our love, our passion. Life is too short to invest in anything for the wrong reasons. I only expect one thing from a founder – that they be impeccable with their word. I can deal with anything else, but I can’t deal with someone that is bad with their word.

VC is not an easy asset class. There is never enough capital, it is illiquid, companies take forever to grow, and there are thousands of reasons why a company will fail. In order to be successful in this asset class you need to put your heart and soul into the process of building innovative companies that are developing products that don’t exist. It’s scary and risky and filled with disappointment at every turn. To last as an early stage investor, you need to love it, otherwise you’ll be miserable.

I love investing in the early stage. I love the companies, I love the entrepreneurs, I love my co-investors (ahem Kirby Winfield ahem). There is nothing more interesting to me than talking investing with other investors. They are my “squad”. They are my tribe. I’ve never felt a sense of belonging in any other walk of life. I want to be a Pro at this, an All Star, a HOFer, the G.O.A.T.

Ascend Founder Profile: Curtis Fonger - Whalesync

This is a series of real talk blog posts meant to let founders share a bit about themselves and their companies without the marketing jargon and “killing it” puffery of most tech startup profiles.

What does your company do, for who, in plain English please!

Whalesync lets businesses automatically sync their data across no-code tools like Airtable and Webflow. This makes it easy to manage things like customer data, marketing campaigns, and blog content spread across their SaaS applications without needing to hire software engineers and build a data pipeline.

What's a typical day like for you, from wakeup ‘til bed?

I wake up at around 7:00am, after which I immediately get a cup of coffee. I'm very much a coffee addict.

My wife and I have two young boys so we spend about an hour getting them dressed and fed. At 8:30am we head out the door and I take the kids to daycare. I then work from home, starting at 9:30am and ending at 5:30pm. The whole team is a virtual space in Gather throughout the day, so I normally work through lunch at my desk.

At 5:30pm I head out and pick up the kids from daycare, head home for dinner, and play with the kids for about an hour until they get ready for bed. After we get the kids to sleep, I either relax or finish up any work I didn't quite wrap up during the day. I finally fall asleep at around 10:00pm–11:00pm.

What keeps you up at night?

On my deathbed, I don't want to think "I regret not doing XYZ." We're only given one life and I want to make sure I do what I'm meant to do.

What brings you joy?

My faith, spending time with my family, and singing in the Seattle Symphony Chorale.

What is one word you hate to hear?

Restricted

What is one word you love to hear?

Opportunity

What was your biggest failure in the past year?

It's hard to think of anything big because we've been very blessed this past year with Whalesync. If I had to choose one thing, it was that we raised a small round right before we were accepted into YC. In retrospect, we should have waited until after we knew our application result before starting a fundraise.

What was your greatest accomplishment in the past year?

I'm not sure if this counts as an accomplishment, but one thing I'm very grateful for was meeting my cofounder Matthew. Rarely have I enjoyed working with someone as much as him.

Who or what inspires you most?

Sara Blakely. She has shown tremendous grit and ingenuity bootstrapping and building her business.

What's your best tool for managing stress?

Spending quality time with my family and getting 8 hours of sleep.

What's getting the most burn on your playlist right now?

Sidewalk Prophets

Favorite shoes?

Flip-flops, because it means that I'm having fun somewhere warm.

Favorite cooking ingredient?

Garlic. Other than dessert, it makes just about anything better.

Portland VC Profile: Julie Harrelson

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

Julie Harrelson has more diverse business experience than the next 3 VCs put together. She brings it all to the table in support of founders, and after working with her on a recent company, I’ve grown to admire her candor and manner - and her business brain!

What made you decide to be a professional investor?

As a former operator who made every fundraising mistake under the sun as an early entrepreneur, I wanted to make investments with founders of seed stage companies to accelerate their success. I also wanted to activate capital in the Pacific Northwest, my lifetime home. Data show that small funds tend to outperform larger funds so we decided to build build small, seed stage funds (approximately $10M-$20M)  and create portfolios of about 25 companies.

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

I've variously been CEO, management consultant and sales and marketing executive. I've worked nationwide with global companies and have a substantial network in the Pacific Northwest. Beyond that I've have been involved in both successful and failed companies, learning from the school of hard knocks and from some amazing colleagues over the course of my career. It benefits founders in that I know their pain from operating experience and can support strategy development and leveraging resources for successful execution.

Why should founders want you on their cap table?

We are active but not activist investors. So we are engaged when you need us but not wasting entrepreneurs time. We are available for the good stuff and the hard stuff. As former operators, we don't freak out when we hear about obstacles--we help to resource the solutions. We strive to be clear, fair and as compassionate as it is possible to be in balancing the dynamic tension of building a successful portfolio and being human. Our diligence process is well-defined and doesn't take tons of founders precious time. Our portfolio founders share best practices and resources with each other.

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

Monthly it varies but somewhere between 200-300 calls/Zooms per year.

How many new investments do you make per year?

5-7

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

Check size is $100-$250K, generally, valuations ar less than $8M, 75% tech of the portfolio is tech, 25% consumer brands.

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

This is like naming your favorite child! Seriously, take a look at the Cascade portfolio.

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

Seattle/PNW will show the same ability to weather the storm and come out better on the other side as it always has. Layoffs and a massive shift in executive leadership plus dynamic industry and world changes could lead to an increased number of startups that try to solve big issues with the PNW leading the way.

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

Mary J. Blige and U2-One.

Favorite shoes?

Toss up between Converse Classic Chuck Taylor All Star high-tops and LaBucq loafers.

Favorite cooking ingredient?

Most used: Olive Oil
Most cooked: Fish of any kind
Most enjoyed: Cake

Seattle VC Profile: Sri Chandrasekar, Point72 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

Sri Chandrasekar, Managing Partner at Point72 Ventures, is a builder at heart. And he’s quietly built a formidable career as a VC, having recently established a Seattle presence for multi-stage fund Point72. He’s a renaissance man and a great guy to grab a glass of wine with. Stoked to have him on the blog.

What made you decide to be a professional investor?

I stumbled into it. I always thought it was far more likely that I’d be a founder than an investor. But I had the opportunity to join In-Q-Tel (the strategic VC arm of the CIA and broader intelligence community) and that was an opportunity I couldn’t turn down. That job got me hooked – every day, I get to talk to people who quit their jobs to start something they are passionate about. There’s nothing more energizing than engaging with founders. 

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

I was an engineer, and still somewhat consider myself one. I spent the formative part of my career building systems for the US Military and Intelligence Community. In my role at In-Q-Tel, the closest analogue to what I did was probably a Technical Product Manager. And that’s what I bring to the table with our founders. I’ve built and shipped products. I’ve had hundreds of conversations with potential customers about their needs and turned that into product features. That experience translates to helping early-stage founders who are facing the same challenges. 

Why should founders want you on their cap table?

We make every effort to support founders who want to go the distance. Because of our team, our experience, and our platform, we believe we are in a strong position to know what ‘good’ looks like from the earliest stages all the way to the public markets. We believe we have designed our fund to support scaling beyond just providing capital. We don’t want to lead your Series A and disappear. We pride ourselves on being value-additive investors. 

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

Talking to founders is in our DNA, so we do a ton of calls. We’re always happy to be available for exciting ideas. 

How many new investments do you make per year?

Over the past three years, we have made, on average, 20-25 investments per year. Our full portfolio can be viewed at https://p72.vc/portfolio/

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

While we focus first on companies raising Seed and Series A capital, our capital is flexible, which gives us the ability to support our portfolio companies through subsequent rounds and find new opportunities with founders who are further along. We have teams investing in several verticals including deep tech, fintech, and enterprise software, and are always looking for bold ideas. 

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

This is too hard! It’s like asking which child is your favorite…

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

I’m very bullish about the opportunity for PNW startups. I think there’s more technical talent here than almost anywhere else in the world.  I’m particularly excited about Cloud, AI, and Space, because I see them all as areas where the Seattle ecosystem has the most expertise, and yet they’re all still in their infancy.  

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

Primarily EDM. My wife recently went to an Alan Walker concert in SF, so let’s go with Alan Walker.

Favorite shoes?

I love British hand-made shoes. And since I don’t dress up very often these days, I love my Crown Northampton sneakers. 

Favorite cooking ingredient?

Eggs. They’re magical and can be turned into everything from breakfast to dinner based on what you make.