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Meet Nazuk Thakkar, the Ripple Investor Who Lifts up Young Founders

January 27, 2025

By: Nate Bek

For young founders, Nazuk (Naz) Thakkar might be your strongest ally — literally. 

In college, she took over a powerlifting club and made it more open to women, sparking her passion for lifting and a drive to make traditionally exclusive spaces more inclusive. That experience shaped her mission: make hard-to-crack communities more accessible. It also gave her the grit to advocate for founders taking their first swing.

“It’s founder empathy,” she tells Ascend. “Running the powerlifting club and also being an active member in this traditionally male-dominated sport taught me how to support people building from the ground up.”

Naz also sees massive potential in young founders. “These young founders are fearless and committed,” she says. “They’re willing to take a bet on themselves, and that energy is what’s going to take their companies far.” 

As an investor at Ripple Ventures, a Canadian venture firm, Naz focuses on high-conviction pre-seed investments, writing checks between $250,000 and $1 million for core deals and $50,000 - $100,000 through Ripple’s Fellow Fund.

Ripple is currently investing out of its Fund III, anchored by the Royal Bank of Canada and the Government of Canada's renewed Venture Capital Catalyst Initiative ("VCCI") through BDC Capital. The firm focuses on companies tackling outdated industries like healthcare, logistics, and construction. 

Naz was kind enough to sit down with Ascend for our VC profile series, where we showcase early-stage investors from across the US. We talked in more depth about her  global roots, her views on young builders, and why sauce is the best ingredient. Read to the end for carve-outs.

*We've edited this conversation for brevity. Enjoy! — Nate 👾


Nate: Thanks so much for doing this, Naz. How did you get started on your journey of becoming a professional investor? 

Naz: I grew up in Ottawa, Canada’s capital, but it always felt like a small town. I literally grew up in farmland, surrounded by cows and horses. Back then, I didn’t know much about startups. My dad worked in cybersecurity, and when I was in fourth or fifth grade, he started his own company. Watching him scale the business and take that chance on himself was exciting and left a lasting impression on me.

Later, my family moved to Singapore, where I did high school. Living there broadened my perspective—I traveled to nearly 40 countries, which shaped my worldview. After high school, I returned to Canada to study business at Queen’s University. The standard career paths—investment banking, accounting, consulting—didn’t appeal to me, which was unsettling because everyone else seemed so sure of their career trajectory.

Some friends in private equity suggested looking into venture capital. It clicked. My dad’s tech background and my exposure to Singapore’s fast-paced innovation ecosystem made VC feel like a natural fit. At 18, I cold-emailed around 100 VC funds during my first semester. One fund, Trend Forward Capital in New York, took a chance on me. I spent 4–5 months there as an analyst, and it blew my mind. Venture capital was the most exciting and dynamic space I’d ever seen. Where I could be myself and thrive. 

You get back from New York and your internship, what do you do from there? 

Back at Queen’s, I helped launch the Ontario chapter of Front Row Ventures (Canada’s version of Dorm Room Fund) and created Queen’s first VC course to make this career path more accessible for students.

To gain operating experience, I became the first hire at a DTC brand in New York called Ruby. I worked on scaling their retail and customer experience operations, handling biz dev and sales. But I missed software and investing. That’s when I came across Ripple Ventures through their fellowship program. I loved their grassroots, operator-focused approach to investing. I pitched myself hard, and they brought me on. Four years later, I’m still here.

You mentioned your operator experience. I worked in retail too — at a fish spot and an ice cream shop. While that doesn’t exactly translate to software, I think there are some shared lessons, like dealing with black swan events and the unpredictability of running a business. As an operator-focused VC, what do you offer founders? Why do they want you on their cap table, both personally and as a fund?

Travel shaped how I work with people. Seeing different cultures and perspectives taught me how humans tick. At university, I accidentally minored in religion because I took so many courses to understand worldviews. That foundation helps build founder empathy and trust, which is critical at the pre-seed stage.

Founders face big risks and uncertainty, and I believe in being a good, kind human first. That’s why they want Ripple on their cap table. We show up—whether it’s answering late-night emails, reviewing decks at midnight, or just listening when things get tough.

It’s about being like a third co-founder, filling gaps and offering support. My own experiences—traveling, being an early operator, and facing challenges—drive that approach. I know how much it matters to have someone in your corner early on.

What are you personally excited about these days? App layer/infra etc.

I spend most of my time around application layer, digging into verticalized applications for cybersecurity and compliance. 

I care most about very clear, immediate and costly problems that are ripe for disruption and have budgets to access with unique distribution advantages. I’ve been seeing a lot of these trends in use cases within gov, pharma, healthcare, climate and fintech especially for example where we've done a few deals this year. 

You’ve done a few deals in Seattle, like Zealot, the spin-out from the University of Washington, and Climba, the agent company. Being based in Toronto, how do you position yourself in that market? And how do you approach competing in larger U.S. markets and winning allocation there?

Starting with Toronto, it’s about building rapport with founders. There’s a risk aversion here that’s more obvious than in SF or New York. But Toronto is getting to a place where founders are more comfortable. There’s a wealth of resources and a strong sense of community, similar to what I’ve seen in Seattle.

You see people co-investing and collaborating on deals. I’m passionate about building that ecosystem in Toronto. I host monthly VC events and spend time in the community building out our co-investor network. The grassroots approach matters. You need founders to trust you, even if they’re not raising today. You want to be their first call when they are.

Toronto founders often take the time to work closely with investors. But the brain drain is real. You have to win on value-add. That’s why Ripple focuses on pre-seed gaps — both capital and domain expertise. We invest in thought leadership, community work, and founder support. That’s where you win in Toronto.

It’s similar to Seattle. We travel to build our co-investor network and think about strategies to help portfolio companies scale. It’s about setting them up to win — not just in Canada, but globally. That means working with VCs who can back future rounds, building corp dev networks, and thinking strategically about what’s next for the companies to scale.

When I was in Seattle, I saw founders building in a space with gaps similar to Toronto’s pre-seed scene. Ascend and PSL are bridging those gaps, keeping founders from draining to SF. It’s all about post-investment work: graduating companies, co-investor networks, corp dev connections, and helping companies succeed beyond just your capital.

Let’s talk about Seattle. We’re a Seattle VC, and, yes, we pander to our audience — people click for that. You’ve been here, hosted an event, and made a few investments. Coming from across North America, what excites you about the opportunities here? AI talent stands out — that’s obvious. The legacy of juggernauts like Microsoft and Amazon is huge. But beyond that, let’s talk about the personality of the founders.

Our most recent investment in Seattle came from students and dropouts from UW. Making that investment, we realized there are incredibly smart kids here who are just building.

They have this “screw it, I’m just gonna build something” culture. It’s not as common in other universities and we need more of that self-commitment.

In Seattle, it’s different. These young founders are ruthless and fearless. They’re willing to take a bet on themselves, and that energy is what’s going to take their companies far. We saw that firsthand with our investment.

Interesting, I don’t hear that often. I’m friends with some of the most cracked young engineers here, and you’re right: they’re killers. Some that come to mind are Caleb, Jamari, and Parsa at our portfolio company Moondream. You alluded to it, but what’s the bear case? 

I think the ecosystem in Seattle, to talk about the bear case, needs to cater more to the young builders. There’s a very strong focus on investing in seasoned founders. We talked a bit about the access gap to capital for early-stage companies, but it absolutely exists for young builders too.

When I was trying to understand what organizations exist within UW and other universities in the PNW, there’s not a lot. But there are these kids who are so inspired. They’re close to SF, so they’re drinking from the firehose, surrounded by all the smart people in Seattle, and they’re willing to build companies.

We’ve spoken to so many who aren’t necessarily looking for capital but for support and value-add investors. The good thing is there’s amazing talent, hustle, and dedication to building here. That’s rare to find outside the traditional tech hubs.

People need to keep an eye on these young builders and pay attention to who’s up and coming, rather than always focusing on three-time exit founders or ex-Amazon execs. The folks coming out of school and building companies are some of the most committed I’ve seen. Turnover and commitment are always challenges for young builders, but what’s coming out of the Seattle schools is very impressive.

I don’t know how much you’ve been following what Kirby has been posting online or some of the things I’ve been involved with, but yeah, there’s a lot happening. There’s DubHacks, CSeed, and YoungTech Seattle. Switching gears, what songs are getting the most run on your headphones? 

My partner had never seen Twilight, so I was like, "Okay, it’s officially that time of the year — we have to watch all the movies." And we did. We binged every single one in a weekend. Since then, the soundtracks have been on repeat. I’m obsessed with "Eyes on Fire" by Blue Foundation —it’s such a classic. I also love all the EDM remixes of it. But in the gym, I’m in my punk rock era. And I’m a dubstep girl through and through — dubstep is my go-to for all my lifts.

What’s your go-to shoe? 

One, lifting shoes—absolutely. My heeled lifting shoes have changed my life. Seriously, I can’t imagine squatting without them. They give you depth, comfort, mobility and the range of motion you need. They’re 100% my ride-or-dies. Day to day, though, I love Nike Blazers. The color schemes are awesome, they look good with everything, and they’re just such a timeless casual shoe. 

Go-to ingredient in the kitchen? 

Oh, okay, I love this question. I’m a big believer that food is just a vessel for sauce. Like, literally, the whole side of my fridge is packed with different sauces—especially hot sauce. I really believe in the power of spice. I’ll add spice to anything. As for ingredients, the trifecta is garlic, onion, and chili. 

Honestly, you can’t go wrong with those.

Tags Ascend, Ripple Ventures, Nazuk Thakkar

Token Talk: Decentralizing AI Compute for Scalable Intelligence

January 22, 2025

By: Thomas Stahura

Compute is king in the age of AI. At least, that's what big tech wants you to believe. The truth is a little more complicated.

When you boil it down, AI inference is simply a very large set of multiplications. All computers do this kind of math all the time, so why can't any computer run a LLM or diffusion model?

It's all about scale. Model scale is the number of parameters (tunable neurons) in a model. Thanks to platforms like Hugging Face, developers now have access to very well performing open source models at every scale. From the small models like moondream2 (1.93b), and llama 3.2 (3b), to medium range ones like phi-4 (14b), and then the largest models like bloom (176b). These models can run on anything from a Raspberry pi to an A100 GPU server.

Sure, the smaller models take a performance hit, but only by 10-20% on most benchmarks. I got llama 3.2 (1b) to flawlessly generate and run a snake game in python. So why, then, do most developers rely on big tech to generate their tokens? The short answer is speed in performance. 

Models at the largest scale (100b+ like gpt4o and the such) perform best and cost the most. That will probably be true for a long time but maybe not forever. In my opinion, it would be good if everyone could contribute their compute to collectively run models at the largest scale. 

I am by no means the first person to have this idea.

Folding@home, launched October 2000 as a first-of-its-kind distributed computing project, aimed at simulating protein folding. The project reached its peak in 2020 during the pandemic, achieving 2.43 exaflops of compute by April of that year. That made it the first exaflop computing system ever.

This also exists in the generative AI community. Petals, a project made by BigScience (the same team behind bloom 176b), enables developers to run and finetune their large model in a distributed fashion. (Check out the live network here.) Nous Research has its DisTrO system (distributed training over the internet). (Check its status here.) And there are plenty of others like hivemind and exo. 

While there are so many examples of distributed compute systems, none have taken off for the reason that it's too difficult to join the network.

I’ve done some experimenting, and I think a solution to this could be using the browser to join the network and running inference using webllm in pure javascript. I will write more about my findings, so stay tuned.

If you are interested in this topic, email me! Thomas @ ascend dot vc

Tags Compute, Token Talk

OpenAI’s o3 model performs well on benchmarks. But it’s still unclear on how it all works.

Token Talk: The Rise in Test Time Compute and Its Hidden Costs

January 15, 2025

By: Thomas Stahura

Reasoning models are branded as the next evolution of large language models (LLMs). And for good reason.

These models, like OpenAI’s o3 and High-Flyer’s DeepSeek, rely on test-time compute. Essentially, they think before speaking by writing their train of thought before producing a final answer. (This type of LLM is called a “reasoning model.”)

Reasoning models are showing terrific benchmark improvements! AI researchers (and the public at large) demand better performing models, and there are five ways to do so: data, training, scale, architecture, and inference. At this point, almost all public internet data is exhausted, models are trained at every size and scale, and transformers have dominated most architectures since 2017. This leaves inference, which, for the time being, seems to be improving AI test scores. 

OpenAI’s o3 nails an 87% on GPQA-D and achieves 75.5% on the ARC Prize (at a $10,000 compute limit). However, the true costs remain (as of Jan 2025) a topic of much discussion and speculation. Discussion on OpenAIs Dev Forum suggests, per query, roughly $60 for o3-mini and $600 for o3. Seems fair; however, whatever the costs are at the moment, OpenAIs research will likely be revealed, fueling competition, eventually lowering costs for all.

One question still lingers: How exactly did OpenAI make o3?

There exists no dataset on the internet of questions, logically sound steps, and correct answers. (Ok, maybe Chegg, but they might be going out of business.) Anyways, much of the data is theorized to be synthetic.

Image credit

StaR (Self-Taught Reasoner) is the subject of a research paper that suggests a technique to turn a regular LLM into a reasoning model. The paper calls for using an LLM to generate a dataset of rationals, then use that dataset to fine-tune the same LLM to become a reasoning model. StaR relies on a simple loop to make the dataset: generate rationales to answer many questions; if the generated answers are wrong, try again to generate a rationale given the correct answer; fine-tune on all the rationales that ultimately yielded correct answers; and repeat.

It's now 2025 and the AI world moves FAST. Many in the research community believe the future are models that can think outside of language. This is cutting-edge research as of today.

I plan to cover more as these papers progress, so stay tuned!

Tags Test Time Compute

Startups backed by Ascend are outlined by a bounding box.

Mapping Seattle's Enterprise AI Startups

December 31, 2024

By: Nate Bek

At the start of the year, we spotlighted Seattle’s understated position as one of AI’s most influential hubs.

Since sharing that market map, the scene has evolved dramatically. A wave of AI startup formation and funding has followed breakthroughs in OpenAI’s GPT models and open-source architectures. Researchers, hyperscaler veterans, and serial founders are stepping away from established roles to launch new ventures.

Funding totals, as in other regions, are skewed by major deals. Dave Clark’s Auger ($100M) and Xaira Therapeutics ($1B). But beneath these outliers, a vibrant ecosystem of early-stage startups is thriving, often backed by top-tier investors

Founders are tackling niche infrastructure challenges and building app-based businesses. The city also spawned AI Tinkerers, now a global network connecting thousands of top AI innovators across more than 28 cities.

Seattle remains an enterprise-focused market. This has sharpened our focus on this market map to highlight B2B AI startups, open-source projects, and products, including: AI Stack, Model Development, Business Operations, Vertical Office Apps, and deskless workforce solutions.

Seattle remains the world’s second-most concentrated market for AI and software talent, behind only the Bay Area. The city’s hyperscalers are investing billions in new data centers, advanced chip development, and hiring top-tier AI professionals. At the same time, OpenAI, Anthropic, Nvidia, Meta, and Google have established satellite engineering hubs in the region, further solidifying its position as a global AI powerhouse.

Despite this concentration of talent, Seattle trails other metros in funding totals as access to local capital lags. Our focus remains on deepening our commitment to the region — fostering connections with local talent and supporting the next wave of transformative companies.


Methodology: Our map highlights companies, products, and projects we view as foundational to the broader development of AI, with a focus on enterprise applications, underlying infrastructure, and models. It features more than 120 logos showcasing the wide-ranging potential of AI in real-world settings. Bounding boxes identify companies we’ve invested in, acknowledging any potential bias upfront. This is not a comprehensive list or a ranking — rather, it’s a snapshot of the region’s evolving AI ecosystem.

Tags Ascend, Seattle AI Market Map

Our 2025 Predictions: AI, space policy, and hoverboards

December 23, 2024

By: Nate Bek

Happy holidays from the Ascend team!

We enter 2025 with big questions on AI’s societal impact, new model breakthroughs, and a wildcard twist:

AI’s Societal Impact: How will AI reshape life as we know it? Will universal AI tutors enter classrooms? Will debates over AI ethics hit the Supreme Court? Will robots finally be… intimate? 

AI Technology Advancements: What’s next for the tech? Will AGI still be a pipe dream, or will we see a breakthrough? Will multimodal models dominate, or will agents take center stage? Could AI-powered apps become more profitable than the underlying models?

Black Swan Event: Anything goes — wild, random, unexpected. Will the Cascadia Subduction Zone finally do the thing? Will Froot Loops get banned under RFK? Will Spokane declare independence and start its own state with Idaho?

Here are our takes:


Kirby Winfield, Founding General Partner

AI’s Societal Impact: There will be at least one drone swarm attack on US soil in 2025. 

AI Technology Advancements: Test-time training will replace pre-training as the standard method of predictive model optimization.

Black Swan Event: The Mariners will win the World Series.

Jen Haller, Partner and Chief of Staff

Societal Impact: We will use AI tools to be more intentional about forming IRL connections with others.

Technology Advancements: This is less of a prediction and more of a wish: My Oura Ring tracks stress, heart rate, and sleep. By 2025, an AI agent should take that data and help manage my schedule. Shift meetings when I’m overloaded, remind me to take breaks, and keep me on track for a balanced day.

Black Swan: I finally get my hoverboard. 

Nate Bek, Associate

AI’s Societal Impact: Fans will appreciate availability over authenticity. AI-generated songs, movies, books, you name it — tuned to an artist's voice and style — will be good enough to be enjoyed by even the most loyal fans.

Technology Advancements: Small models will win the enterprise.

Black Swan: RFK will ban Froot Loops.

Thomas Stahura, Software Engineer

AI Societal Impact: Image-to-video will be the go-to meme format of 2025.

AI Technology Advancements: Coders will consume at least half of all generated tokens in 2025.

Black Swan Event: The outer space treaty of 1967 will be renegotiated.

Tags Ascend

Meet Tyler Churchill: From CAA to finding Startup Talent in Seattle for Bonfire Ventures

October 24, 2024

By: Nate Bek

Tyler Churchill  knows how to spot talent. Before he got into venture capital, he was at CAA, one of Hollywood’s top agencies.

“I definitely see a lot of parallels between CAA and VC,” Tyler tells Ascend. “Finding the next great actor is not so different from identifying a strong founder.”

More than anything, Tyler believes in a mentality of being a trusted partner in building and creating, stepping into whatever role is needed to ensure success. At the heart of this is understanding that the founder is the driving force, while he and others provide the scaffolding (cast and crew)  to bring their ambitious vision to life.

Bonfire Ventures is a Los Angeles-based Seed-stage venture fund focused on B2B startups, investing from its $168 million third fund. The firm manages more than $1 billion in assets. 

Tyler was kind enough to sit down with Ascend for our VC profile series, where we showcase early-stage investors from across the US. We talked in more depth about his VC passion, Bonfire’s focus on B2B applications, and what connects Hollywood to startup investing. Read to the end for carve-outs.

*We've edited this conversation for brevity. Enjoy! — Nate 👾

Nate: We’ve talked before about your move up from LA. I know you're representing Bonfire in the PNW, including your recent Supio deal—congrats, BTW! Can you share why and how you became a professional investor and what brought you to where you are now?

Tyler: I went to USC for undergrad, thinking I wanted to get into the business side of entertainment. I’ve always loved film, so after graduating, I joined CAA, working in the motion picture talent / lit departments. It was a super interesting experience, and after a couple of years, I went to work for one of our production company clients. I was there for a little over a year and got to work on the fourth season of Eastbound & Down with HBO. 

But while I was working in entertainment, most of my friends were moving to the Bay Area and getting into tech. The more I caught up with them, the more I wanted to make the jump into software. So I moved up to the Bay and got an early sales role at a bootstrapped software company called TechValidate, learning sales on the job. My experience at CAA translated well to software sales since both are very consultative and service-oriented.

TechValidate eventually sold to SurveyMonkey… How did that change your trajectory? 

TechValidate was eventually acquired by SurveyMonkey for nearly $100 million, and I stayed there for a while. But I missed the startup environment and wanted to learn more about building and scaling a company, so I joined a venture-backed startup called EverString. 

This was a big shift from TechValidate’s bootstrapped approach — EverString had raised a lot of money from Lightspeed and Sequoia and later raised a Series B. I helped build out the mid-market sales motion, and EverString eventually got acquired by ZoomInfo.

During this time, I got exposed to the VC world, hanging out with people in both startups and venture capital. I became fascinated by the shift from solving specific problems at a startup to addressing challenges across multiple startups as an investor. It seemed like a great way to apply a broader, more strategic lens.

Two acquisitions later, how did you manage to break into VC? 

I saw business school as a chance to manufacture an inflection point, so I went to Chicago Booth for my MBA. During the summer between my two years, I interned at Bonfire Ventures and kept working with them throughout my second year. I helped portfolio companies refine their models for Series A, sourced interesting companies, and stayed close to the team, showing my commitment to the firm. Eventually, I got an offer from Bonfire before finishing my MBA, and after graduating, I moved back to LA. I’ve been with Bonfire ever since and it’s been an awesome ride.

You invest at the seed stage, so let’s start with Bonfire's focus—specifically the verticals. I know it's primarily B2B software, but what are you focusing on now? Is it still the AI application layer, or are you looking beyond that, maybe into more traditional data? And what are you most excited about in the coming months?

Sure, I’ll break it down into the key areas we're focused on, and I'll speak for myself here too. Bonfire is entirely focused on B2B—though not just SaaS. We invest in FinTech and other B2B models, but our sweet spot is seed-stage B2B. For us, that means some early commercial traction, typically around $300K to $500K in annualized revenue. We usually write $2M to $3M checks, leading a $3M to $5M seed round.

We focus mainly on the application layer. While we’ve done dev tools, infrastructure, and API-based investments, most of our expertise lies in understanding market-specific pain points and how applications can solve those challenges and improve workflows. We’ve had a lot of success in vertical software, which is still a big focus area for us. We think there’s a significant opportunity here, especially in applying AI to specific industries where domain knowledge and understanding the nuances of end users and stakeholders are key.

We’re particularly excited about applied AI and how it integrates with vertical software. It’s not just about adding AI but knowing where it adds real value, which requires a deep understanding of users and customers. That’s where we feel we can make a difference—helping founders apply AI in ways that matter, refine the messaging around it, and build out the GTM processes and motions that help them reach short term milestones but more importantly lay the foundation for a healthy, scalable and efficient business. In vertical software it’s especially gratifying because many of these customers are SMBs or mom-and-pop businesses, the backbone of the economy, and most to none have the means of building things internally like software businesses. Helping them leverage AI and better software feels like a meaningful mission.

So we’re diving deep into vertical applications and applied AI across industries right now. It’s exciting work, and it feels like a great opportunity to make a real impact.


Jerry and Supio are great examples of that focus. Legal is such a clear use case for applied AI—there’s a lot of repetitive, time-consuming work that AI can streamline, especially for clerks and junior legal staff. It’s about making their workflows more efficient so they can focus on higher-value tasks. 
He represents the perfect founder archetype in vertical software where you need to be extremely customer-centric — listening to them, talking to them constantly, and certainly loving them. But you also need to become an expert yourself and be able to challenge them and introduce new ideas. Customers are great at telling you their problems - they are not great at articulating solutions. 

It’s not just about giving them what they say they want; you have to challenge them, too. That’s been an interesting dynamic to learn, and Jerry really embodies it well with incredible empathy and and energy.

I saw that firsthand when moderating the panel with Jerry. It’s interesting—I hadn’t heard “challenge and love” used with customers before, but I like it, especially for a tough industry like legal. It makes sense. Switching gears, what drew you to Seattle after LA, the Bay Area, and Chicago, beyond the nature? How do you see the technical talent and opportunities here, especially at the application layer?

The catalyst for moving here was family — my wife is from the area, and we always felt a pull to come back at some point. It wasn't clear when it would happen, but after our twins, Hayden and Charlotte, were born three and a half years ago, we realized we needed more space and family support. My team at Bonfire was very understanding and flexible, even though I’m the only one up here while the rest are in SoCal. It made sense for the business too — having a presence in the Pacific Northwest.

The ecosystem here is really exciting, with deep technical talent that’s no longer just concentrated at Microsoft and Amazon. There are many promising B2B software companies of substantial scale, and the technical and commercial talent pool is incredibly deep and growing quickly. The AI talent here is particularly strong, creating a lot of momentum in that category.

It’s a great time to be a seed investor in this region. We focus on later seed rounds but like to get to know founders early. Being here allows us to have those initial conversations, help with whiteboarding, introductions, etc and build relationships over time—so when they’re ready to raise a seed round, we’re already on board and there is a trust-based personal relationship underlying the diligence process. 

Do you have concerns about Seattle’s startup scene? Enterprise software dominates, and there’s talk of over-investment in AI, not a lot of venture capital, and limited go-to-market talent. What’s your take on the risks here?

I don’t think the concern around over-investment in AI CapEx is specific to Seattle; that’s more about where revenue opportunities will emerge to justify those asset valuations. My main concern is that Seattle’s ecosystem is still developing—similar to LA. It takes time and effort to build a network like San Francisco, New York, or Boston. And leveling up the region just takes dedication, intention and faith in what your community is capable of, but the PNW is incredibly deep here. People up here believe this can be among the biggest hubs for innovation, especially when it comes to AI.

The focus should be on creating networks where technical founders can meet go-to-market co-founders, innovative ideas can and chaotic serendipity can be fostered and harnessed. There’s a lot of energy and action in the veins of Seattle — look at what Aviel and others are creating with Foundations to build connectivity. People are fired up about it. 

Fun question time… What’s your favorite shoe? 

Running a lot and loving the Reebok Floatzig Symmetros.

What song is getting the most play? 

Still Hot by Nic D and Connor Price to get me going for early AM workouts, and anything from Zach Bryan. 

Love it. Zach Bryan’s “Sun to Me” has quickly become one of my favorite songs of all time. What ingredient is your favorite?

We eat a lot of salmon in our house, so probs have to go with that. And we have three kids now so fruit pouches I guess. 

Seattle! 

Tags Tyler Churchill, Ascend, Bonfire Ventures

Getting Unstuck: Insights from Dave Hersh, Founder of Jive Software, Turnaround Expert

October 21, 2024

By: Nate Bek

It’s easy to fall in love with building a company. There’s a problem to solve, an ocean to boil. But soon, the startup path shows itself — a winding road filled with unexpected potholes and distractions.

Sometimes, you just get stuck.

Dave Hersh knows that feeling. He built Jive Software and took it public, but the push to scale and meet expectations came at a price. He has since gone on to work in venture, private equity, and now helps transform stuck companies. 

“At Jive, we went from being focused on innovation to operating for quarterly numbers,” he says. “That's when the slow death began.”

Founders often feel the need to prove themselves. Hersh was no different. 

“I was insecure and scared of trusting my intuition,” he says. “I thought, ‘If I lose, I’m worthless. So anything to avoid that’” 

This drive to win can lead to short-term decisions that create long-term issues: launching products too soon, scaling too fast, raising too much, and telling investors a story that’s a bit too rosy.

“There's this belief that success means raising a lot of money fast, growing quickly, and chasing a big market,” Hersh says. “Those are the things I pursued. But looking back, it turned out not to be the case, and it sowed the seed of destruction for me and many others.”

Hersh recently joined Ascend for an AMA, a monthly session where portfolio founders hear from experts. He shared lessons about avoiding false stories, knowing when to grow, and trusting your gut. You can find the full audio recording here — Passcode: wGgU&.86

False Narratives Can Sink You

Founders often shape stories to raise money, but those narratives can come back to bite. They set unrealistic expectations with investors and then scramble to meet them, losing sight of what the business actually needs.

As Hersh puts it, “You’re raising the money on a false narrative, and that false narrative belies a deeper truth, which is, you don’t have market pull yet.”

Focus on aligning your story with reality, not just what you think investors want to hear.

Scale Responsibly

Scaling prematurely can be a costly mistake. Hersh tells the story of Docsend in his book, a company that raised $8 million and jumped into aggressive growth. The strategy ended up backfiring.

“They described it like trying to play a golf tournament with clubs that were half the size,” he says.

The company couldn’t compete effectively and burned through cash chasing larger competitors until they went back to their roots, got lean and focused, and rebuilt the organization around their superpower. And a few years later sold to Dropbox at a large valuation. Scaling should be a response to real demand, not a decision driven by available capital. Make sure your clubs are ready before you take on the course.

Avoid Raising Too Much Money Too Soon

Venture capital isn’t the enemy, but too much, too early, can be destructive. Founders sometimes raise large rounds of funding before fully validating their product, which creates pressure to grow faster than is feasible.

“Most of the money in VC is made from 10% of companies being profoundly successful,” Hersh says. “But for the individual founder, you don’t have a portfolio — you have your one company.”

This creates a misalignment between founder and investor timelines. While investors are betting on many companies, founders are betting on one. Be patient, raise only what you need, and don’t let the funding drive your strategy.

“Stay leaner longer, find market pull, and then raise when it’s irresponsible not to,” says Hersh.

Focus on value creation, not vanity metrics. 

Metrics can be a trap. It’s easy to get lost chasing numbers that look impressive in a pitch deck — user counts, downloads, glowing reviews. 

“I spent so much time hacking soft metrics,” he says, “but none of that moved the needle for the business.”

Stick to Your Core

A founder’s intuition is the most critical, and most undervalued asset.

Hersh reflects on this, saying, “if I had just been able to develop my intuition, been more strong in my conviction... as the founder, as CEO, you have more information than anybody else, and you understand narratively how it all fits together on a larger scale.”

Tags Dave Hersh, Ascend, Jive Software

Mapping Seattle's Active Venture Firms

October 2, 2024

By: Nate Bek

Take a tour of Seattle’s active venture firms, curated by Ascend.

Tags Ascend, Seattle Venture Capital

PHOTOS: Founders Bash 2024

September 16, 2024

Browse our collection of photos from Founders Bash 2024! :-)

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Tags Ascend, Founders Bash

VC for the rest of us: A big tech employee’s guide to becoming startup advisors

September 5, 2024

By: Nate Bek

Talk to any startup expert about building the next Silicon Valley, and they’ll often point to one key element: a strong pipeline of seasoned advisors. 

Startup advisors are trusted guides who bring wisdom and insight to the ridiculously tough journey of building a business. They offer strategic advice, share hard-earned lessons, and provide mentorship that goes far beyond simple guidance. Advisors are sounding boards for ideas, connectors to crucial networks, and steady hands in times of uncertainty. A great advisor can be a kingmaker.

For those in big tech or engineering roles outside the startup ecosystem, breaking into advisory roles can be challenging — there can be broad gaps between the networks of people who’ve spent their careers in companies that have already scaled, and those of serial entrepreneurs and startup founders. 

Typically, these gaps are filled by institutional matchmakers — programs designed to connect founders with aspiring mentors. 

In Seattle, Techstars served as one of those intermediaries. It brought together tech leaders, former founders, and investors. Its final “Mentor Madness” event paired 211 mentors with the 24 startups in its cohort, and nearly 350 mentors were listed on its website. No other local program operates at that scale today (although Foundations aims to help fill that void).

Techstars excelled at transforming casual introductions into lasting advisory relationships, helping a number of Seattle startups grow. The program provided structure and guidance for mentors, supported by resources like David Cohen’s Mentor Manifesto.

Now, with Techstars out of Seattle, the way startup advisors connect with founders has slowed. 

The shift raises a big question: How do we continue to support the Seattle startup ecosystem with a steady flow of new advisors? 

We’ve created an FAQ for big tech professionals interested in upholding the region’s robust mentor network. We gathered insights from both seasoned and emerging advisors.

Here’s what we learned:

  • Advising startups offers a chance to stay at the cutting-edge while sharing valuable experience. For many, it’s about being part of the journey, helping others overcome challenges, and staying connected to the pulse of new ideas and technologies. 

    Advisors are rarely in it just for the money, though equity packages and cash compensation are common.

    Taylor Black, a Director on Microsoft's Incubation Studio & Strategic Programs Team and former B2B SaaS founder, says he’s driven by the thrill of working with early-stage companies. 

    “I love the zero-to-one space, getting from idea to product-market fit and all the questions that come with it,” he says. 

    With experience in deep tech, consumer, and platform technologies at Microsoft, Black has guided hundreds of startups through those critical first steps. The motivation is the excitement of turning ideas into reality and solving the puzzles that come with it. 

    David Pitman, a former staff engineer at Google Cloud and exited founder, says advising is about giving back. 

    “I got a lot of great mentoring and advising when I was a founder,” he says. “Some of those people are still my mentors today.” It’s a way to pay it forward, sharing hard-earned wisdom and staying connected. 

    Pitman adds that advising can be a two-way street: “You can rapidly build up a lot more knowledge about, say, how the current funding environment is going.”   

  • Aseem Datar, vice president of next-gen computing and AI platform at Microsoft and a former Madrona Partner, says it’s important for you to find “advisor-founder fit.” 

    • Stage: Figure out which stage of the startup’s lifecycle best fits your skills. If you’re like Black, that’s at the very early stages when the company is developing a product. But for others in big tech, it might make more sense to work with a later-stage company that found product-market fit and is looking to scale.

    • Value add: Determine the types of problems a founder might have, and how your unique skill set fills that gap. This could be customer intros, technical advice, supply chain support, culture and internal processes, and more. 

    • Goals and financial situation: Some startups don’t have the cash on hand to pay you right away, or at all. Others might want to pay you and not want to give you equity for your help. The ideal situation is a mutual agreement with the founder and a genuine desire to help, which rewards a secondary bonus to you “picking up the shovel” and actually helping the startup grow. 

    Jim Alkove, founder of a cybersecurity startup and advisor to several others, says that you should start with determining your “why:” What do you want to achieve? And where can you offer the most value?

    Black’s advice is straightforward: “Go for it, but be honest about what you’re good at. If you haven't built something from zero to one, don’t advise on that. Instead, focus on what you really know — whether that’s Kubernetes, C++, or setting up strong dev environments.”

  • Becoming an advisor is much like finding a new job. Begin by building a strong network and offering your help before officially taking on an advisory role to establish your value. 

    Connections with venture capitalists and startup studios can increase your visibility to startups. In relationships to both founders and their investors, offer customer introductions, even for companies you don’t plan to work with long term. Also offer your expertise as a trusted third-party reference. Alkove notes that he spends a significant amount of time on quick reference checks and technology due diligence, sometimes more than on customer intros. 

    He adds that his portfolio of advisory roles came from three key sources:

    1. Echomark: Had an existing relationship with the founder, a former colleague at Microsoft.

    2. Safebase: Spent time with the team and offered help, eventually joining as advisor.

    3. Ambit: Was introduced through his relationships with venture capitalists.

    Alkove says the most important aspect is spending time with the team. Understand their culture and product to see where you fit in and jump on opportunities to help. 

    There are also existing programs that you can join that serve as intermediaries:

    • For hardware-focused startups, Amish Patel launched Conduit Venture Labs’ Fellows. Taylor Black is a fellow there, and I wrote the story for GeekWire here. 

    • For women-led companies, Seattle-based Graham & Walker has its Catalyst program (Jen Haller and I participated as mentors in its most recent Cohort).

  • When pitching yourself as an advisor, avoid positioning it as a pay-to-play network. Customer intros are important but should be done thoughtfully and with credibility. They should also be just one of many tools you offer to founders.

    For Alkove, his value lies in his CISO connections. As a former executive at Salesforce, he was the buyer of cybersecurity tools, which enabled him to advise on how product pitches would be received. 

    “If you’re the ideal customer profile, that's valuable,” he says.

    Pitman, drawing on his experience from Google Cloud and multiple startups, highlights the broad applicability of lessons learned in building from zero to one and thousands to billions. 

    His experiences with software, UX, and AI can help new tech companies avoid costly mistakes they have to unravel after they start rapidly growing post-Series A. 

    “The advantage of an advisor is having someone who can help you see ahead to the next stage of your company before you get there, basically giving a superpower to see into the future,” he says.

    However, he cautions against applying big tech solutions to startups without considering their practicality. “If you can't come up with a realistic way that some small startup is going to be able to put your advice into action, it's probably not that useful for them,” he says.

    Black combines his founder experience and legal background to excel in the zero-to-product-market-fit stage. He has worked in three venture studios, launching startups in deep tech, consumer tech, and platform at Microsoft. Black focuses on testing, ideation, and gathering data for product-market fit. He also uses his legal expertise to craft B2B contracts, which are crucial for refining a product and achieving product-market fit.

    Programs like Conduit Venture Labs' Fellows program works with tech leaders to help hardware-focused startups avoid common pitfalls such as high burn rates, supply chain issues, and limited venture capital interest.

  • When diligencing startups, start with traditional factors: market potential, team background, product viability, and investors. These metrics provide a foundation, but to achieve advisor-founder fit, Pitman looks deeper into his relationship with the founder and the practicality of their professional alignment. 

    “I really want to understand as rapidly as possible if I can actually give useful advice,” he says. Pitman is cautious of founders who claim everything is perfect. “If you think your startup is doing great, you either got that lottery ticket—congrats—or, like most founders, something is always going wrong.”

    To test the relationship, Pitman offers a small piece of advice early on and watches how founders respond. “I want to know this is going in a productive direction and not just giving advice that goes nowhere,” he says. 

    But Pitman is careful not to overstep: “I’d be more concerned if a startup took my advice without seeing it as one data point among many.”

  • Most enterprise professionals seek engaging and interesting opportunities outside their day job, with equity and cash often being secondary concerns—or not a concern at all. Their main motivation is to participate in something exciting beyond their regular work.

    Many advisory engagements don't involve equity, especially when facilitated through platforms like incubators. Black, for example, offers startups around five one-hour sessions initially. After that, he prompts them to decide whether to formalize the relationship.

    The choice between equity and cash depends on the advisor’s goals and the length of the engagement. Black advises opting for equity in long-term engagements due to its potential and crisp alignment with the startup's own fortunes. For short-term projects or one-off contributions, cash might be more practical. In early-stage startups, particularly those transitioning from zero to one, equity is often preferred over cash given the startup’s limited resources. 

    Equity pricing can be difficult to standardize, but resources like the Founder Institute’s FAST template provide a framework. An advisor dedicating at least 20 hours a month to an early-stage startup might expect around 1% equity.

  • Best practices start with connecting deeply with the team. If you’re a tech expert, engage with the engineers. Understand their challenges. Your job is to answer questions and ask the right ones, exposing areas for growth. Think of it as being on a board, but without the voting power.

    Stay “operationally disconnected.” Offer advice with phrases like, “If I were in this situation…" Founders will make mistakes — let them. The key is to help them learn from those mistakes without stepping in too much. As an advisor, your main job is to provide input and ask good questions, which can expose areas that the founder can focus on developing. Be socratic but also supportive. 

    “It’s important to let go of your ego when becoming an advisor — empathy and experience result in the best wisdom,” Alkove says. “In the end, it can be a voyage of personal discovery and growth.” 

    Your pitch as an advisor should be about the full spectrum of value you provide, not just access.

    Pitman brings lessons from extreme sports to advising. He knows the importance of realistic advice. The goal is to help founders push beyond their comfort zones. 

    “You want them to get to the next stage, so offer your expertise to help them achieve that,” Pitman says. “Talent only takes them so far.”

Nate Bek is an associate at Ascend, where he screens new deal opportunities, conducts due diligence, and publishes research. Prior to that he was a startups and venture capital reporter at GeekWire.

Disclaimer: The information provided here is for educational and informational purposes only. It does not constitute financial advice, and you should always consult with a qualified financial professional before making any investment decisions. Past performance is not indicative of future results.

Tags Ascend, Startup Advisor, Jim Alkove, Aseem Datar, Taylor Black, David Pitman, Techstars Seattle
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