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Investing in Yoodli

May 21, 2025

By: Nate Bek & Kirby Winfield

Today, we’re excited to announce our follow-on investment in Yoodli, the enterprise platform for AI roleplays. Neotribe Ventures led the $13.7 million Series A, joined by our friends at Madrona, Cercano, and AI2. 

We navigate the most important moments in life through conversation: closing a sales deal, interviewing for a job, or even prepping for a first date. Clear communication is often the difference between success and missed opportunity.

But most modern tools designed to improve our communication skills fall short. Corporate training still leans heavily on static formats like slide decks and recorded videos, which do little to build the real-time reflexes that define high-stakes conversations. These methods offer information, but they don’t develop skill.

Yoodli is one of the first-movers in a crop of companies innovating in this arena. Through its AI roleplays, users can rehearse high-stakes scenarios, receive real-time feedback, and improve with repetition. It’s an experiential learning tool built on a modern generative AI stack. As Founder Varun Puri puts it, “Yoodli is the batting cage before the big game — but for communication.”

Yoodli started as Project Speakeasy, a lightweight NLP tool that tracked filler words. But it has since evolved into an enterprise platform used by companies like Google, Databricks, RingCentral, Snowflake, BDO, and the University of Washington. These organizations use Yoodli to onboard employees faster, improve sales performance, and reduce the coaching burden on managers and administrators.

Rochana Golani, Databricks’ VP of learning and enablement, told The Information that one-on-one coaching is too expensive and that listening to call recordings doesn’t offer the personalized feedback employees need. Databricks, which employs thousands of sales reps, is now one of Yoodli’s largest enterprise customers.

We invested because we believe Yoodli fits squarely within our SaaS 3.0 thesis — B2B AI applications that target specific workflows and pain points with measurable impact. Communication is an overlooked domain in enterprise software. It’s critical to sales, management, and leadership, yet historically hard to train and assess at scale.

The rise of generative AI has changed that. AI roleplay is a new category that is quickly gaining traction. Salesforce, Gong, and Microsoft are all building in adjacent areas. This validates the space but also signals competition ahead. Yoodli’s edge lies in product depth, speed of iteration, and early enterprise traction. (Read Varun’s take on the competition here.)

We’ve supported Yoodli, a Seattle startup, since its first institutional round in 2022. Kirby met Varun through the AI2 Incubator and wired one of the first checks into the company. Varun previously worked with Sergey Brin at Google and brings the same level of focus to building his team. Co-founder Esha Joshi was a product manager at Apple and brings strong operational depth.

The use cases for Yoodli continue to expand. Sales enablement, manager training, leadership development, performance reviews, public speaking, media training, healthcare simulations — all benefit from practice-based learning. Roleplays can be tailored by persona, difficulty level, language, and feedback style, making them flexible and effective.

With the new funding, Yoodli will grow its team across sales, customer success, and engineering, while deepening its technology to make roleplays more realistic and personalized. You can find those jobs as they go live on the Ascend Job Board. Since our first investment, we’ve helped place multiple team members and advised through early product evolution.

We’re proud to have been early investors in Yoodli and look forward to supporting the team as it grows.

The Information first reported the round, followed by additional coverage in GeekWire.

Tags Yoodli, Ascend, Funding

Generating substantial portions of a codebase with AI could make it harder to protect that software, legal experts say. 

You Let AI Help Build Your Product. Can You Still Own It?

April 10, 2025

By: Nate Bek

Startup developers should treat their AI coding assistants as copilots, not autopilots.

That’s my biggest takeaway from CenterForce’s Governance & Strategy Summit, held Wednesday at Bell Harbor International Conference Center on a sunny day in Seattle’s Belltown neighborhood. In a room full of legal minds from across the country, my goal was to take away what matters most to startup founders working with AI.

Two high-profile AI legal battles framed most of the discussions on stage: one centered on patents, the other on copyright.

In the patent case, computer scientist Stephen Thaler challenged the U.S. Patent and Trademark Office after it refused to grant patents for inventions created by his AI system. In the copyright case, artist Jason M. Allen sued the U.S. Copyright Office after it denied protection for an award-winning image he generated using AI.

“We have some information from cases that are in different contexts, where multiple humans are debating who is an author of a work,” said Eric Tuttle, a partner at Wilson Sonsini, speaking on stage in a session titled “Copyright in the Age of AI: Navigating New Frontiers.”

Courts are likely to use that standard as a starting point, but how it applies to AI-generated content is still unclear.

Brian McMahon, senior copyright counsel at Microsoft, emphasized a practical takeaway from the latest copyright guidance. While prompts alone are not eligible for copyright, there may still be a path to protection if human input shapes the final result.

“As a company, if you're using the AI tool in your business, so long as you’re not just cranking out the output, throwing that into the stream of commerce… and you're instead taking that extra step and modifying the output in some way, I think that's a good opportunity,” McMahon said.

He explained that if a human’s expressive contribution can be detected in the AI-assisted output, that work may qualify for copyright protection.

Tuttle then raised a key concern for software companies. If AI tools are generating a significant portion of your code, can that code and the software built from it be protected under copyright law? That’s still an open question that has not yet been tested in court, he says.

For startup founders building with AI, I believe this is the crux. If your AI system is generating code, how much of it can you actually claim? How much human input is required before that code becomes yours?

At this moment, I asked the panelists to double-click on this point: If you're a startup, the whole ethos is to move fast, break things. So, then, what is your pro bono advice with AI coding tools? Is it to not move so fast using Cursor or GitHub Copilot that you put yourself at legal risk? Or is it to just be aware of these cases making their way through the legal system and continue building fast with AI?

Here’s what they told me:

Tuttle said AI is being widely adopted and it is unrealistic to expect developers to avoid tools that improve efficiency when writing code. He emphasized the importance of understanding the risks that come with relying on AI, especially in the context of intellectual property.

When it comes to copyright, Tuttle warned that generating substantial portions of a codebase with AI could make it harder to protect that software. He encouraged founders to consider other ways to safeguard their work, such as intellectual property protections, technological measures, and contracts.

Tuttle pointed to the idea of “autopilot” versus “copilot.” The more humans are involved in revising, editing, integrating, and making decisions about the code, the stronger the case for authorship. He added that being able to document that human input could be important if the code ever becomes the subject of a legal dispute.

Glory Francke, head of privacy and data protection officer at GitHub, advised founders to pay close attention to the tools their developers are using.

She recommended sticking with commercially offered versions of AI tools rather than free ones. Commercial tools are more likely to protect user privacy by not retaining prompts or using them for training.

Francke also urged teams to review and configure their settings carefully. For instance, some tools allow you to block code suggestions that match publicly available code, preventing them from being used in completions. Others offer code referencing features that show the origin of suggested code and its license.

Francke encouraged teams to “get to know your admin” and make use of those settings to reduce risk and stay compliant.

While much about AI is still unknown and outside of our control, Francke said companies can take practical steps now by choosing the right tools, using the right settings, and making sure prompts are not being used for training if that is not the company’s intent.

“Use the tools that are there to help protect against the harms that you're concerned about,” Francke said.

Jonathan Talcott, shareholder at Buchalter, stressed the importance of understanding open-source licensing when using AI coding tools. He advised companies to put systems in place to manage open-source compliance, whether through features built into tools like GitHub Copilot or external scanners like FOSSA.

“You want to be making sure that you have some type of tool in place,” he said, to track and address licensing issues before they become legal problems.

On the topic of IP and copyright ownership for AI-generated code, Talcott said much is still uncertain and will depend on how current legal cases are decided.

“That’s going to be impacted by how these cases play out,” he said.

Still, Talcott echoed what others on the panel made clear. Avoiding these tools entirely is not a realistic option for software startups.

“Unless you want to be left behind,” he said.

Disclosures: I’m no lawyer, and this isn’t legal advice. The speakers quoted here also made clear they were speaking for themselves, not their respective companies. Ascend is a client of Wilson Sonsini.

Tags Ascend, Coding Tool, CenterForce

Investing in Avante

April 8, 2025

By: Kirby Winfield & Nate Bek

Today, we’re excited to announce our investment in Avante, the infrastructure layer for modern employee healthcare benefits. Fuse led the $10 million Seed round, joined by HighSage Ventures. 

The employer-sponsored benefits market is under strain. HR teams are overwhelmed by administrative work, forced to navigate legacy tools that were never built for today’s demands, while employees are making high-stakes healthcare decisions without the information they need. The current ecosystem relies on a patchwork of point solutions that fail to integrate or scale. 

U.S. employers spent more than $1.3 trillion on healthcare last year, making it the second-largest expense after payroll. Despite its size, this market remains under-innovated and inefficient. Benefits are just too important — too expensive — to be run on spreadsheets and outdated portals.

Rohan D’Souza, Avante’s CEO and co-founder, came to us with a clear read on the market. He had spent months in the field talking to customers, brokers, and benefit administrators. The feedback was consistent. Teams want better insights, more automation, and a way to deliver a high-quality benefits experience without adding headcount.

Rohan’s findings align with what we’ve seen. In a survey of VC-backed startups with ties to Seattle, nearly all reported offering health benefits as soon as they raise a priced round. Coverage is table stakes, even for teams under 10. At larger enterprises, the problem only compounds. Dozens of vendors, thousands of employees, and increasing compliance demands create an environment where small inefficiencies turn into massive operational and financial drag.

Company leaders know it matters — for recruiting, retention, and employee well-being — but the infrastructure to support that coverage is often shallow or nonexistent. 

Avante is building the operating layer companies will need to respond to these pressures. The platform unifies critical data across claims, vendors, costs, and employee engagement. It gives employers a complete, real-time view of their benefits program and helps them make smarter decisions. From plan design to vendor selection to wellness initiatives, everything is surfaced through a single interface with AI-powered insights at the core.

The result is a more scalable benefits operation that improves outcomes for employees and drives efficiency for employers. Avante automates support, integrates cleanly into existing systems, and captures employee sentiment to identify gaps and inform strategy.

We invested, in part, because we believe this team is uniquely positioned to build this product and go after this market. 

  • Rohan previously served as Chief Product Officer at Olive AI, where he played a key role as the healthcare tech company scaled to a $4 billion valuation. 

  • He’s joined by Co-founder Carly Eckert, MD, Ph.D, an epidemiologist and former EVP at Olive, who now leads innovation and impact at Avante.

  • Kabir Shahani, executive chairman, founder of Amperity, one of Seattle’s most successful enterprise startups.

  • Nick Cecil, founding head of engineering, brings deep technical expertise from his time as director of software engineering at Salesforce

This is a rare combination of healthcare fluency, product rigor, and enterprise software execution.

With the funding, the team is looking to expand across key functions. Avante is recruiting for five positions: Senior Product Manager, Head of Revenue, Software Engineer, Junior Software Engineer, and Analytics Engineer. All roles are live on the Ascend Job Board.

We believe Avante will define a new standard for how companies manage and deliver employee benefits, and we’re proud to be a supporter from day one.

Tags Avante, Ascend

Photos via Human[X]

Dispatch from the Desert: Human[X], Robotics, and the AI Power Shuffle

March 31, 2025

By: Nate Bek

Vegas felt like an odd place for a conference about intelligence. The artificial kind, or otherwise. But maybe that made it the right setting.

The slot machines never stopped blinking. The escalators kept funneling us between velvet-curtained ballrooms and DJs and mimosa towers to the floor of a city built to overwhelm. There’s something about putting thousands of people in a place designed to keep you distracted — and asking them to think about the future.

Human[X] was the first AI conference of its kind, but it didn’t really feel like a debut. It felt more like a checkpoint. I came in with a few themes top of mind: robotics, AI labs turning into real institutions, and how venture is reacting to the next wave. Those threads ended up tying most of the sessions I attended together.

From left: Hugging Face, Co-founder; Rachel Metz, AI Reporter at Bloomberg; Arthur Mensch, Co-founder & CEO at Mistral AI; and Metz.

The most grounded — and maybe most striking — observation came from Thomas Wolf of Hugging Face.

"I'm pretty sure 2025 is going to be the year where robots start to work."

Not in theory. In kitchens. In warehouses. On wheels. Reinforcement learning breakthroughs are beginning to land outside the lab, and there’s a new confidence about it. He also flagged what’s missing: openness.

“They're all closed-source… In the future, where robots are everywhere, I would love a part of them to be open so that we know exactly what's inside. Maybe we even build them ourselves."

That tension came up in other corners, too. Brad Porter, founder of Collaborative Robotics, was clear about the practical challenges of humanoid robots. Drawing on his time at Amazon:

“We needed robots that could work collaboratively in and around humans. It was not clear how you were going to safety rate these 300-pound mechanical things that can fall over really easily."

What stood out to me was how rarely this kind of specificity comes up in general AI discourse. These weren’t hypotheticals. They were design constraints from people who’ve already tried and course-corrected.

Alfred Lin of Sequoia framed it well — almost offhandedly:

“The desert is not designed for humans. Just like highways and space.”

Form should follow function. The future of robotics may feel novel, but its success will come down to how it adapts to spaces we already occupy.

From left: Mike Krieger, CPO at Anthropic; Moderator: Alex Heath, Deputy Editor at The Verge; and Kevin Weil, CPO at OpenAI.

Mistral’s session with Arthur Mensch made this shift clear. He spoke about deploying vision models on the edge.

“When the robots [are] in the outer world, it won’t have a very strong connection… you want to have low-latency decision making.”

It’s a reminder that not every AI breakthrough lives in the cloud. Edge environments are where robotics will have to operate, and some of the more forward-looking labs are already planning around that.

He also spoke about Mistral’s recent partnership with Helsing, and the demand for sovereign infrastructure in Europe:

“There's a lot of demand to have a regional cloud because that brings more sovereignty and leverage from an economic perspective… As it turns out, we're pretty good at operating GPUs.”

Labs are becoming more than R&D centers. They’re shaping policy, forming defense partnerships, and influencing national strategies.

Anthropic’s Mike Krieger talked through another facet of this transformation — the delicate balance between building products and staying aligned with partners:

“I called basically all of our leading coding customers to give them a heads up that we're launching Claude Code… We're hearing from people using both.”

He was transparent. It was a small window into what it takes to navigate product expansion when your customers are also your ecosystem.

There was a lot of quiet confidence in the VC session with Navin Chaddha, Lauren Kolodny, and Martin Mignot.

“We're still not at the peak of the hype cycle,” said Chaddha. “VCs have enough money.”

He cited $307 billion in dry powder. Valuations, in his view, still have room to move. LPs remain focused on DPI. “It’s a financial services business,” he said toward the end — a reminder that beneath the storytelling, this is all still portfolio math.

Martin Mignot pointed to the upside:

“We can have trillion dollar VC-backed companies when they go public… A lot of value is being captured by VCs.”

The liquidity window may be narrow, but the bets are only getting larger. And many of them are moving into real-world infrastructure — robotics, autonomy, defense. 

In between sessions, I kept thinking about how far we’ve moved from the “chatbot moment.” Human[X] was filled with serious people talking about serious problems. Model architectures were mentioned less than operational realities.

Vegas was a strange backdrop. Too loud. Too bright. Too artificial. But also kind of perfect. A place built on simulation, where beneath the surface you start to feel what’s real.

Tags Human[x], Las Vegas, Ascend, AI

Token Talk: Open source won the AI race

January 30, 2025

By: Thomas Stahura

If it wasn’t clear already, open source won the AI race. 

 To recap: Deepseek R1 is an open-source reasoning model that was quietly launched during the 14 hours TikTok was banned. The reasoning version of Deepseek V3, Deepseek R1 performs at o1 levels on most benchmarks. Very impressive and was reportedly trained for just $6 million, though many are skeptical on those numbers. 

 By Monday, a week after R1 launched, the model caused a massive market selloff. Nvidia lost $500 billion in value (-17%), the biggest one-day selloff in US history, as the market adjusts to our new open-source reality.

 So, what does this mean? 

For starters, models have been commoditized. Well-performing open-source models at every scale are available. But that’s besides the point. Deepseek is trained on synthetic data generated by ChatGPT. Essentially extracting the weights of a closed model and open sourcing them. This eliminates the moats of OpenAI, Anthropic, and the other closed source AI labs.

 What perplexes me is why Nvidia got hit the hardest. The takes I’ve heard seem to suggest it’s the lower costs it took to train Deepseek that spooked the market. The thinking goes: LLMs become cheaper to train, so hyperscalers need fewer GPUs.

 The bulls, on the other hand, cite Jevons’ paradox. Wherein, the cheaper a valuable commodity becomes, the more it gets used.

 I seem to be somewhere in the middle. Lower costs are great for developers! But I have yet to see a useful token-heavy application. Well maybe web agents… I’ll cover those in another edition!

 I suspect the simple fact the model came out of China is what caused it to blow up. After all, there seems to be such moral panic over the implications on US AI sovereignty. And for good reasons.

 Over the weekend, I attended a hackathon hosted by Menlo where I built a browser agent. I had different LLMs take the pew research center political topology quiz. 

 Anthropic’s claude-sonnet-3.5, gpt-4o, o1, and llama got outsider left. Deepseek R1 and V3 got establishment liberals. Notably, R1 answered, “It would be acceptable if another country became as militarily powerful as the U.S.” 

During my testing, I found that Deepseek’s models would refuse to answer questions about Taiwan or Tiananmen square. In all fairness, most American models won’t answer questions about Palestine. Still, as these models are open and widely used and used by developers, there is fear that these biases will leak into AI products and services.

I’d like to think that this problem is solvable with fine-tuning. I suppose developers are playing with Deepseek’s weights as we speak! We’ll just have to find out in the next few weeks…

In Token Talk Tags Ascend, Token Talk, DeepSeek

Investing in Oumi

January 29, 2025

By: Nate Bek & Kirby Winfield

Today, we’re excited to announce our investment in Oumi, an open-source AI platform. Venrock led the $10 million Seed round, joined by Plug and Play and Obvious Ventures. 

AI is at a critical juncture. Industry leaders are investing heavily in proprietary systems, with OpenAI’s $500 billion Stargate initiative serving as a clear example of the growing shift toward closed ecosystems. These walled gardens centralize innovation and resources, restricting access for much of the AI community.

Even within so-called open-source initiatives, transparency remains incomplete. Models like DeepSeek and Llama provide open weights, but fail to include critical elements such as full training pipelines, preprocessing code, and detailed data provenance. This lack of openness limits developers’ ability to reproduce results, refine models, or push the boundaries of what is possible. Without full access, innovation remains stifled, and the barriers to entry for AI development stay high.

A step-function change is needed to redefine what open-source AI can and should be. Oumi is addressing this challenge by building a fully open-source platform for large foundation models that spans the entire AI development lifecycle: data preprocessing, pretraining, fine-tuning, evaluation, and deployment. By providing access to every component, Oumi empowers researchers and developers to collaborate and innovate without restrictions.

Oumi partnered with more than 13 universities, engaged 36 AI researchers, and built a team of 10 high-profile builders to bring its vision to life.

Our conviction in Oumi was solidified through conversations with CEO Manos Koukoumidis. He has a track record of leadership at hyperscalers like Google, Meta, and Microsoft, paired with academic rigor as an MIT and Princeton PhD. Open collaboration on this scale requires not just technical excellence but strong leadership. Oussama Elachqar and the other seven co-founders were also stellar. It’s rare to find such an exceptional founding team on day one. 

“To protect their interests, closed vendors openly brag about how many GPUs they have in their attempt to secure their compute ‘moat,’” Manos says. “But I believe an open community can do at least as well as them. I actually think it can do a lot better.”

This vision aligns with and helps inform our AI Fast Follower thesis. The economics of AI development have shifted significantly. GPU arbitrage, open frameworks, and pre-trained models have slashed barriers for new entrants. Fast followers can achieve frontier-level model performance without relying on the deep pockets of the early movers.

That said, open source isn’t without its challenges. Monetization can be tricky, and aligning a decentralized community takes effort. But the potential payoff is enormous: a truly global effort driving better, safer, and more reliable models across every modality and use case.

Oumi’s platform is already addressing critical needs in industries where trust, reliability, and scalability are non-negotiable. This progress makes a strong case that open-source collaboration can deliver better, faster, and more inclusive innovation than walled gardens.

We’re excited to share the cap table with notable angel investors including Ruslan Salakhutdinov (Carnegie Mellon professor), Ragavan Srinivasan (Meta Product VP), Vipul Ved Prakash (Together.ai CEO), and Clem Delangue (Hugging Face CEO). 

Open-source AI has the potential to lift all boats, driving global progress and opportunity. Oumi embodies this belief, and we are proud to support their journey.

Tags Ascend, Oumi, Oumi Funding, Open-source AI Startup, Manos Koukoumidis

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

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
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