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Cambly grew from our language-learning experiences. We studied in the U.S., traveled widely, and found immersion teaches faster than classrooms. We wanted a friendly person to practice with, not a formal lesson, and the world mainly seeks to learn English. We built Cambly around one-on-one speaking and focused on English because that's the global demand. My four years at Google shaped my data-driven mindset: build software at scale, run plenty of A/B tests, and let data decide when intuition may misfire. Fundraising was hard early because Cambly is unusual: two Americans building an English-learning platform for billions who don’t speak English, a problem investors rarely see. We chose paid usage as our North Star, measuring actual minutes tutors teach and students learn. When fundraising stalled, we executed Plan B: become cash-flow positive within months, raise margins, offer longer upfront plans, and keep a lean team wearing many hats. We believed sustainable growth beats reckless expansion, and cash flow clarity eased later fundraises. As a leader, I prize ownership and autonomy, while speed must balance with careful planning. The hardest stretch was the failed Series A, which forced us to align the team around cash flow. Hiring country managers taught me to value depth, leadership, and culture.

Jesse Proudman discusses Strix Leviathan, a hedge fund he co-founded three years ago, focusing on defensive crypto strategies that aim for better risk-adjusted returns. The fund seeks to capture 60-70% of gains in bull markets while limiting losses in bear markets, appealing to family offices and high-net-worth individuals. Proudman introduces Makara, a consumer-facing technology platform designed to simplify crypto investment for a broader audience. Makara, registered as crypto's first robo-advisor, offers thematic investment baskets based on user interests, aiming to educate and engage new investors. Proudman emphasizes the importance of SEC registration for credibility and transparency in the crypto space. He contrasts the current market dynamics with 2017, noting that institutional acceptance has changed the landscape, leading to quicker recoveries from dips. He believes the asset class is here to stay, despite ongoing regulatory challenges and market volatility. Interested individuals can learn more at makaradigital.com and strixfund.com.

Elias reflects on Drift, calling it the biggest failure of his life and describing the sting of losing relevance after bringing in a new CEO and management. He explains that startups demand resilience and that rewarding detail and vanity metrics—carrots, candy bars, trophies—made his public company path untenable. He says Drift failed not for lack of customers but for speed and execution, and he admits that selling to private equity changed his sense of identity and purpose. He discusses the paradox of caring and not caring, explaining that as an entrepreneur you learn what you truly care about. The interview covers the belief that the life of an entrepreneur is hard, that immigration into the US opened doors to opportunity, and that the single biggest constraint for incumbents is organizational inertia. He argues the future favors smaller teams and compute-enabled productivity, not thousands of managers; big players like Google struggle to move as fast as startups. On hiring and management, Elias details his intense style: high agency criteria—IQ, grit, execution speed, obsession—and onboarding new hires in a day with a live coding test. He contrasts hire-fast, fire-slow with hire-slow, fire-fast, and emphasizes gut-level fit, not titles. He reflects on family life, marrying early, having three kids, balancing personal life with intense work, and the idea that you can pursue both family and entrepreneurship, though it’s often ugly. Regarding finances and strategy, he notes that cash flow and profitability now matter more than pure growth, and that smaller, AI-assisted teams may replace heavy labor budgets. He discusses VC dynamics, selling, and his preference for building rather than running a VC firm. He remains optimistic about culture, craftsmanship, and the possibility of better products and customer relationships, expressing a broader hope for art, family time, and human connection in a tech-driven world.

In this live Q&A episode, Chris Koerner hosts multiple callers with diverse, real‑world business challenges, focusing on entrepreneurship, due diligence, and growth strategy. Tiffany explains how she purchased a merchandise and screen‑printing business only to discover after closing that key facts, including employees, revenue, and equipment, were misrepresented. She recounts training gaps, ongoing vendor issues, mounting debt, and a looming lawsuit as she contends with declining revenue and mounting interest on credit cards. Chris guides her through potential paths, balancing immediate operational needs with longer‑term options, such as potentially selling the business, pursuing bankruptcy, or aggressively rebuilding revenue through targeted marketing, outsourcing, and cost reductions. The discussion emphasizes the importance of realigning expectations with reality, validating business fundamentals, and learning from the misrepresentation to minimize future risk. Tiffany’s scenario highlights a broader theme: when a business is misrepresented at acquisition, the responder’s job is to help assess viable near‑term actions and realistic longer‑term trajectories, including how to salvage value, renegotiate vendor terms, and strategically market to winning customer segments while containing burn rate. The host also explores practical remedies for a damaged cap table and stressed operations, advocating a careful balance of cost discipline, revenue growth, and prudent legal steps while acknowledging the emotional toll of a difficult business situation. Across different callers, the show shifts toward general startup playbooks: how to assess market opportunities, how to size addressable markets, and how to test ideas with limited spend. Michael, seeking to buy or build a pack‑and‑ship business, receives a structured framework for market saturation analysis using Outscraper data, zip‑code demographics, and competitive benchmarking; Corey’s kayak‑dock idea and stadium locker concept prompts a feasibility to focus on scalable, outsourced execution rather than heavy upfront inventory; Stephen’s automation‑first approach to replacing Zapier with a custom platform prompts a discussion on market segmentation, onboarding, and the tradeoffs of servicing small customers versus targeting high‑value enterprises; and Romel’s underwriting AI co‑pilot offers a glimpse into niche SaaS development and market entry strategies in complex industries like insurance. Overall, the episode converges on actionable, incremental steps for ambitious founders facing practical constraints and competitive pressure.

The best way to do deals is to do what we call a deal. The business needs to be so simple I can explain it to grandma. Terms control the price. Learn about the language of business so deeply that it becomes a fluency. Women currently only make up 2% of the business acquisition buyers in America despite 40% of women actually owning businesses. Amjad Masan wants to create 1 billion coders, and he challenges the audience, 'Why are you only trying to create 1 million owners?' 'The only thing that really matters in due diligence is two things if you're buying a company.' 'Are the numbers real? Because we buy we don't buy hopes and dreams. We buy realities and cash flow.' We buy profitable cash flowing day one. The business has to be in existence for more than 5 years. The business has to be profitable. The business needs to be so simple I can explain it to grandma. The last thing is I want to be curious about it for at least a few years. The anti-signal would be, 'This business doesn't make me any money right now, but it's going to grow a ton.' 'We had just given them $25 million, and it was me and some partners.' They were out of cash. 'They had completely financially cooked the books.' The accountants were in on it, the regional banking partner was in on it. We ended up turning the business around. Money's a cruel mistress. Don't fall in love with something that can't love you back. We built what I think is the best acquisitions and business buying community and education curriculum in the world, called the contrarian community.

In this episode of The Koerner Office, the hosts and callers dig into practical advice for growing and operating service-based businesses, with a strong focus on how to handle payments, acquisitions, and client outreach. The discussion begins with a tactical question about invoicing and collecting payments for a B2B publishing services provider. The consensus emphasizes moving away from pure handoffs of bank information toward a formal payment processor setup. Options discussed include Stripe for its robust recurring features and, as a cheaper alternative with a more complex front end, Authorize.net paired with a gateway like HoneyBook. The dialogue highlights interchange-plus pricing as a transparent model, noting its typical impact on debit cards versus credit cards and the hidden margins many big providers enjoy. The participants also consider easier, low-friction paths such as using Card (CAR-RD) or PayPal, and even creating a simple invoicing flow via Upwork or HoneyBook to send customers a payment link. The takeaway is to implement a system where invoices are easily generated and paid online, even if the business currently operates without a website. As the conversation broadens, a second thread centers on starting or growing a service business using a lean, test-driven approach. Callers discuss testing verticals for a cold email agency that connects staffing and recruiting firms with businesses needing specialized talent, including concrete advice on campaign structure, daily email volumes, industry targeting, and metrics interpretation. Chris and participants stress the importance of real, money-on-the-line proof of concept over vanity metrics like open rates, and recommend running parallel campaigns across multiple industries to identify the best fit before scaling. A third thread explores strategic due diligence for acquiring a physical-services business, such as an espresso catering venture or a roofing operation. The host cautions about owner-dependency risk, recommends a formal operating agreement and potential mediator, and suggests a staged transition to reduce customer churn. Several callers offer practical tips on sales staffing, referral strategies, and finding initial customers, including direct outreach, targeted lists, and even humorous direct-mail tactics to prompt action. The episode closes with encouragement to test and validate ideas through conversations with potential customers before committing capital or time to unproven ventures.