Pour Over

Deferred's Judd Schoenholtz on Scaling, Velocity as a Moat, and more Startup Truths for Today’s Founders

Why Deferred Exists: Judd explains how he discovered the world of 1031 exchanges and why he and his co-founders saw an opportunity to modernize it. Flipping the Revenue Model: Deferred chose a no-fee approach, shaking up the standard where legacy intermediaries charged fees and quietly profited on customer funds. Building with Three Co-Founders: Hear how the trio now divides responsibilities. Each operates with autonomy in their lane, but with collaboration as a force multiplier rather than a bottleneck. Startup Truths: Why questions centered heavily on acquisitions and exits, despite them being only a small part of startup life. Judd talks about how ironic this is, since acquisitions happen late and often involve stress, not just success stories. Lessons from Exits: He unpacks why founders should not sell too quickly and why some sales are necessary or strategic, but the mindset should always be to continue the grinding. Templates Over Shortcuts: Learn why there are no tricks or hacks to building a company and why Judd is in favor of structured processes that save time and drive decision-making. Corporate VCs and Strategic Capital: Explore the pros and cons of corporate venture capital. Hear why, although today’s terms are cleaner, founders must time it carefully, tie investments to commercial relationships, and ensure rights do not restrict future options. Evolving Capital Markets: How the funding environment has transitioned into smaller early rounds, larger late-stage bets, and changing revenue expectations, with AI and fintech sometimes raising earlier on technical merit. Velocity as Moat: Reasons for Deferred’s approach to defensibility, which is built on speed and depth of customer understanding, and how the company creates a product experience and efficiency that are hard for others to replicate. Scaling Growth: How Deferred provides commercial brokers with a scalable channel by running experiments to test growth strategies. He also breaks down why “peanut-buttering” efforts across too many marketing channels is a bad approach.  Choosing Design Partners: The best design partners are not always the ones that look optimal on paper. They explain why partners who are collaborative, responsive, and willing to provide valuable feedback should be prioritized.  Advice for Founders: Takeaways on building through rapid shifts and why founders should not chase shortcuts. Remember that companies usually fail by giving up, not because of competition.   QUOTES “[The co-founders] all kind of have our own lanes, and what that does is allows us to go as fast as possible – and be incredibly productive.” “There really are no hacks [for building a business]. You can’t really shortcut doing hard work and getting better at things over time.” “Don’t try to re-invent the wheel. Follow best practices and try to create templates for these different things around recruiting and fundraising. You want to live your day with an open schedule and try to focus on the things that matter.” “Make sure that the [marketing channel that] you go one-hundred percent in on is as scalable as you need it to be.”  “The ability to know your customer and build for them quickly is a differentiator against the pace of everything else changing.”   LINKS MENTIONED IN THIS EPISODE Deferred [https://www.deferred.com] Judd Schoenholtz on LinkedIn [https://www.linkedin.com/in/juddschoenholtz/] Arteen Arabshahi on LinkedIn [https://www.linkedin.com/in/arteeninla/] Fika Ventures [https://www.fika.vc/] Subscribe to Fika’s Newsletter to receive Pour Over Episodes [http://eepurl.com/iaoksz] You’ve been listening to “Pour Over” presented by Fika Ventures. Fika is an LA-based early stage venture fund investing in b2b companies across North America. If you enjoyed this podcast and have suggestions for future guests, or general thoughts and feedback, feel free to email us at info@fika.vc [info@fika.vc]. Thanks for listening.

Altitude and Advertising: Building MNTN with a Pilot’s Precision and a Hollywood Twist with Mark Douglas

From eHarmony to Advertising Mark kicked off his career as a software engineer and unexpectedly made his way into advertising through a stint at eHarmony, where the focus was matching people with other people. Years later, it clicked for him that the same kind of logic could be applied to matching consumers with the right products. That insight ultimately became the foundation for MNTN. Today, MNTN helps small and mid-sized companies tap into streaming TV for performance marketing. TV used to be a playground for big-budget advertisers. MNTN has changed that by bringing digital-style targeting and measurement to the medium. “I don’t think of it as advertising. I think of it as helping passionate founders get their product seen by the right people.” Enter Ryan Reynolds The Ryan Reynolds story is classic LA. Mark met Ryan from a mutual connection and gave him a demo of the platform. After a mutual introduction, Mark gave Ryan a demo of the platform. The very next day, Ryan called and asked if he could come onboard. “He called me the day after we met and said, ‘Can I be your Chief Creative Officer?’ Of course I said yes.” Since then, Ryan has been all in. He takes sales calls, leads creative efforts, and helps shape the brand’s direction. And it’s working. Today, 75 percent of MNTN’s revenue comes from inbound leads, compared to just 2 percent three years ago. AI as a Flight Director, Not a Replacement AI is fully embedded into how MNTN operates. It helps with everything from product matching and copywriting to press release generation. AI supports the team, but decisions still rest with the humans. “Our goal is to build AI like a flight director. It suggests the best path, but people are still in control.” This approach allows the company to grow efficiently. The sales team hasn’t expanded in three years, and engineering will soon make up half the company. AI gives the team extra lift without adding weight. Building a Remote Culture That Actually Works MNTN became fully remote during the pandemic and decided to stick with it. Team members now live all over, including cities like Miami, Napa, and Bend. Instead of having a central office, the company brings everyone together three times a year in cities like Aspen, Chicago, and New Orleans. “It costs millions of dollars to bring 500 people together for a few days, but it’s worth every cent.” To stay coordinated, everyone works on LA hours. MNTN also offers monthly three-day weekends and vacation stipends that increase with tenure. Mark emphasized that culture is not built on perks alone. It is about mutual respect and building a relationship that people want to be part of. “Most jobs feel transactional. We want MNTN to feel like a relationship you actually want to be in.” Flying High, Literally A standout moment from the talk was Mark revealing that he flew himself to the retreat from Miami. He’s a licensed pilot and logs nearly 400 hours in the air each year, which is about the same as many commercial pilots. “Flying clears my mind. At 40,000 feet, you’re fully present. It’s like a spa for the brain.” That mindset has shaped how he approaches leadership. Just like with autopilot in a jet, he believes in setting smart systems that run the day-to-day while keeping leaders ready to step in when needed. Eyes on the Horizon As the session wrapped up, Arteen asked what many were wondering. Is an IPO on the way? Mark shared that while MNTN initially filed an S-1 but held off due to market conditions, he couldn’t share more at the time of First Look. The company officially debuted on the NYSE on May 22nd, 2025, marking a significant milestone in its journey and for Los Angeles. In Q1, MNTN reported 47% year-over-year growth, making it the fastest-growing company in its category. “We feel ready. And we’re just getting started.” LINKS MENTIONED IN THIS EPISODE Watch the live keynote video at First Look [https://vimeo.com/1091901008] MNTN [https://mountain.com/] Mark Douglas on LinkedIn [https://www.linkedin.com/in/teachmehow2douglas/] Arteen Arabshahi on LinkedIn [https://www.linkedin.com/in/arteeninla/] Fika Ventures [https://www.fika.vc/] Subscribe to Fika’s Newsletter to receive Pour Over Episodes [http://eepurl.com/iaoksz] You’ve been listening to “Pour Over” presented by Fika Ventures. Fika is an LA-based early stage venture fund investing in b2b companies across North America. If you enjoyed this podcast and have suggestions for future guests, or general thoughts and feedback, feel free to email us at info@fika.vc [info@fika.vc]. Thanks for listening.

More Than a Fleet: Motive’s Mission to Redefine the Physical Economy with Shoaib Makani

From KeepTruckin to Motive Shoaib kicked things off with a story about the company’s original name, KeepTruckin. He admitted it might have captured the early energy of the team, but it quickly became clear that the name didn’t match the scope of what they were building. Even in the early days, customers were coming from industries beyond trucking, including oil and gas, field services, and passenger transit. They eventually rebranded to Motive in 2022, aligning the name with their broader vision. Motive’s mission now spans the full spectrum of the physical economy serving over 100,000 customers. From construction and logistics to energy and public sector work, the company builds tools that help physical operations improve safety and productivity. “Anybody who moves things or builds things in the real world can benefit from what we’re building.” — Shoaib Makani, co-founder and CEO, Motive From One Product to a Platform Motive’s early success came from its fleet management product. That momentum gave the team the confidence to expand into new problem spaces. But scaling into a true platform came with lessons. Shoaib shared that one of his biggest early mistakes was stepping too far away from product. Eventually, he came back in as head of product and pushed for a higher bar across the board. “The CEO has to be the head of product for whatever is the leading edge of the platform. Otherwise, you will lose to the CEO who is.” That renewed focus helped Motive go from good to great. The company’s driver safety product now leads the market and sets the bar for what’s possible with AI and camera-based monitoring. Betting on Hardware Motive didn’t set out to build hardware. Shoaib admitted they initially tried to integrate with third-party devices. That changed quickly. They realized that in order to deliver a truly differentiated product, they needed to control the full stack. “If you want to be 10x better, you have to own the entire experience. That meant learning how to build hardware ourselves.” Today, Motive designs and builds its own dash cams, asset trackers, and sensors. Shoaib sees hardware as a competitive advantage that will only grow more important as software becomes easier to build with AI. The hard-won skills around manufacturing, logistics, and supply chain are now giving Motive an edge in solving problems at the intersection of hardware, software, and AI. Scaling with Focus With more than 100,000 customers and over a million drivers using the platform, Shoaib reflected on how the company’s scale has changed how they operate. One of the biggest challenges now is focus. Customers request hundreds of new features, and it would be easy to build reactively. But Shoaib stressed the importance of making room for long-term bets. “You have to solve today’s problems, but also plant the seeds for tomorrow. If you don’t, your growth will eventually stall.” That forward-thinking mindset is what has enabled Motive to keep compounding, even at scale. Shoaib shared that he’s already thinking about product lines that could be generating hundreds of millions in a few years — and how to start building them now. AI Done Right AI has become a hot topic, but Shoaib made it clear that Motive has been investing in it long before it was trendy. Their AI-powered driver safety product is a standout example. The company trains models to detect unsafe behavior like drowsiness, phone use, and close following. That data translates into real outcomes, like an 80 percent reduction in accidents. “We’ve been working on this since 2017. It’s not a feature. It’s a core part of what we do.” He also emphasized that AI is only one piece of the puzzle. Selling into the enterprise still requires great go-to-market execution and thoughtful product marketing. It took years to build the muscle, but now the team is focused on using that foundation to bring new AI-driven products to market. Leading from the Ground Floor Shoaib talked openly about his leadership style and how it has evolved. Though he started his career in venture capital, he made a conscious decision to become a deeply hands-on operator. He stays close to the things that matter most and expects the same from his team. “The best work happens when we shine a light on it together.” He’s also created a culture where people are encouraged to push back. Motive, he said, is a place where you can tell the CEO he’s wrong — and be heard. Surviving the Hardest Year One of the most powerful moments came when Shoaib shared a near-death experience for the company. In early 2017, three years in and still pre-revenue, the team was out of cash and struggling to raise more. A regulatory shift in the trucking industry was about to create a wave of demand, but investors weren’t buying it. At the last minute, Scale Venture Partners stepped up and funded the round. That year, Motive went from zero to $27 million in ARR. “It was a real bet. But we knew what was coming. We just needed the runway to get there.” What’s Next Motive has since raised more than $560 million and continues to see rapid growth. But Shoaib is still energized by the problems ahead. The team is now working on how to shift from perception to control — moving from just monitoring behavior to taking real-time action in the physical world. “Our customers want automation. They see us as their on-ramp to AI. That’s the future we’re building toward.” LINKS MENTIONED IN THIS EPISODE Watch the live keynote video at First Look [https://vimeo.com/1091905216] Motive [https://gomotive.com/] Shoaib Makani on LinkedIn [https://www.linkedin.com/in/smakani/] TX Zhuo on LinkedIn [https://www.linkedin.com/in/tianxiangzhuo/] Fika Ventures [https://www.fika.vc/] Subscribe to Fika’s Newsletter to receive Pour Over Episodes [http://eepurl.com/iaoksz] You’ve been listening to “Pour Over” presented by Fika Ventures. Fika is an LA-based early stage venture fund investing in b2b companies across North America. If you enjoyed this podcast and have suggestions for future guests, or general thoughts and feedback, feel free to email us at info@fika.vc [info@fika.vc]. Thanks for listening.

Reimagining Contracts and LegalTech with Min-Kyu Jung

Founder Journey: Min-Kyu started as a corporate lawyer in New Zealand, drawn to deal-making over litigation. While he enjoyed the challenge, the manual nature of contract work frustrated him, sparking the idea for an AI-driven solution. He began coding Ivo himself before moving to Silicon Valley to scale the company in a faster-moving, high-growth environment. New Zealand vs. Silicon Valley Startup Culture: In New Zealand, calling yourself a founder felt equivalent to being unemployed—the startup scene lacked excitement. In contrast, Silicon Valley thrives on innovation. Min-Kyu found a community that embraces ambition, urgency, and big ideas, making it the perfect place to build Ivo. Ivo’s Unique Offering: Unlike DocuSign, which focuses on signing contracts, Ivo tackles the hardest part—getting contracts ready to sign. The AI legal assistant redlines, reviews, and negotiates contracts directly in Microsoft Word, using customized playbooks to align with each legal team’s preferences. Inspiration Behind Ivo: Ivo is named after Saint Ivo of Kermartin, the patron saint of lawyers, reflecting the company’s mission to serve legal professionals with intelligence and precision. AI Applications, GPT Wrappers, and Frontier Models: Min-Kyu pushes back on the idea that AI legal tools are just thin GPT wrappers. Ivo is deeply integrated into legal workflows, offering more than AI-generated text by embedding customization, domain expertise, and adaptability into the product. Technological Advancements and Adaptability: With models like DeepSeek emerging, startups must stay agile. Ivo is designed to be model-agnostic, ensuring it evolves with AI advancements rather than being tied to a single model like GPT. Ivo’s Roadmap: Ivo takes a forward-looking approach, anticipating where AI will be in 6-12 months. As models become faster, smarter, and cheaper, Ivo positions itself to lead the evolution of AI-powered contract negotiation. The Future of Ivo and Contract Law: Min-Kyu predicts that contracts will move beyond lawyers, allowing business professionals to negotiate agreements themselves. AI will streamline legal work, shifting lawyers’ roles from manual reviewers to strategic overseers. Key Values at Ivo: Ivo hires people who are intelligent, fast-moving, conscientious, and deeply invested in their craft. The team prioritizes execution over perfection, embraces problem-solving, and takes pride in building a transformative product. Hiring Generalists vs. Specialists: While lawyers bring industry expertise, generalists add fresh perspectives. Ivo blends specialists who understand legal pain points with generalists who drive innovation. Leadership Style: Min-Kyu is hands-on, high-expectation-driven, and values ownership. As Ivo scales, he aims to foster a culture of speed, adaptability, and high standards while empowering his team to lead.   QUOTES “[In New Zealand] I was almost too embarrassed to tell people that I was founding a startup because I knew people wouldn't really understand what I mean by that.” “In the Bay Area, I feel like everyone has this very keen sense of excitement about building and creating new things, and people don't get bored when I go on long rants about my opinion on some tech thing.” “The hard part about signing a contract is getting the contract to a point where it's ready to sign in the first place.” “I think founders in the space do have to be willing to really rip everything up as technology improves.” “I think it's important to not be too tied to a single model, and be willing to make the product fixable enough to accommodate different ones.” “I like to hire people who are who are intelligent, who value speed, who are conscientious, who have the quality of being – ‘relentlessly resourceful.’”   LINKS MENTIONED IN THIS EPISODE Ivo [https://www.ivo.ai/] Min-Kyu Jung on LinkedIn [https://www.linkedin.com/in/min-kyu-jung/] Min-Kyu’s Blog Post - 'You Should Move to San Francisco' [https://www.minkyujung.com/posts/sanfrancisco] John Chen on LinkedIn [https://www.linkedin.com/in/johnchen12/] Fika Ventures [https://www.fika.vc/] Subscribe to Fika’s Newsletter to receive Pour Over Episodes [http://eepurl.com/iaoksz] You’ve been listening to “Pour Over” presented by Fika Ventures. Fika is an LA-based early stage venture fund investing in b2b companies across North America. If you enjoyed this podcast and have suggestions for future guests, or general thoughts and feedback, feel free to email us at info@fika.vc [info@fika.vc]. Thanks for listening.

Revolutionizing the Employee Experience in the Age of Connected Benefits with Shannon Goggin

Early Lessons & Shannon’s Motivations: How far you can get if you have a high level of ambition and are willing to challenge what is commonly accepted as impossible. Working at Zenefits, Shannon was able to see the blockers behind accessibility before landing on the need for new infrastructure.  Early Challenges & Building a Trusted Brand: Noyo Aims to demystify the world of benefits to empower everyday people through a data-based approach. Earning trust and building relationships in an environment with a high volume of sensitive and private information isn’t as easy as it looks in retrospect. Scaling a Team: Growing from three employees to 80, the highest performers take ownership of what they are hired to solve for. They are hyper-collaborative, hyper-creative, and work to form a point of view.  Finding Identity & Character of Leadership: A personal identity rooted in the company’s evolution propels Shannon to commit fully to her team, partners, and the mission of the country. Her passion for understanding the details to shape the path forward where the data is so clear and reliable that users can easily benefit.  Sources of Inspiration: Identifies that no one person can be your model for success, but rather believes that different styles are necessary in different moments.  Changes in Data: A surge in investment for those building in the tech startup space, with a broader set of companies playing in the space. Insurance companies investing in APIs and considering the future to a new extent.  Long-Term Vision: Now supporting the biggest insurance companies in the world, a future focus is on helping to transform their own systems. Using technology to scale, not people, and working to support the customer base.  Bridging the Gap to the End User: Everyone who works at Noyo is an end customer with their own insurance, which enables them to fully understand the experience.   QUOTES “That heightened level of ambition and just being a little stubborn, you get a lot farther than most people think is possible.” “We’re not trying to burn down the industry; we’re not trying to blow it up and start it over. We’re trying to really work with people who are already in the industry to make it dramatically better.” “For me, understanding the details is what helps me shape how we get the path forward.” “The challenge for us is, how much good data can we get from the insurance companies to help them improve? So we are investing a ton to add new software tools to improve the quality of data and visibility.” “[It] always surprises the partners we work with for the level of scale and service we provide them, which is a testament to the software that we have built.” “When you’re building something; when you’re shipping something, think about yourself as the end user because you are.”   LINKS MENTIONED IN THIS EPISODE Shannon Goggin on LinkedIn  [https://www.linkedin.com/in/shannongoggin/] Noyo [https://noyo.com/] TX Zhuo on LinkedIn [https://www.linkedin.com/in/tianxiangzhuo/] Fika Ventures [https://www.fika.vc/] Subscribe to Fika’s Newsletter to receive Pour Over Episodes [http://eepurl.com/iaoksz] You’ve been listening to “Pour Over” presented by Fika Ventures. Fika is an LA-based early stage venture fund investing in b2b companies across North America. If you enjoyed this podcast and have suggestions for future guests, or general thoughts and feedback, feel free to email us at info@fika.vc [info@fika.vc]. Thanks for listening.