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.