Penelope Talbot-Kelly

Great conversations at our WillowTree Ventures dinner with leaders across fintech and AI. A few themes stood out strongly: enterprises are leaning into AI for real efficiency gains, product and engineering orgs still set the agenda, and the whitespace in “boring” industries is wider than most people assume. It’s clear that the next breakout companies in AI for financial services won’t come from the obvious places. Thanks to everyone who joined - excited to keep working alongside founders building in these non-obvious, high-impact wedges.

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I had the opportunity to speak to the CEOs of the startups funded by Shift4Good, which is investing in sustainable transportation. In full disclosure, I chair their impact committee. I argued that firms should think about scaling deep (building stronger relationships in existing communities), rather than simply thinking about scaling fast (wide geographical spread). Research by Suntae Kim and Anna Kim shows that scaling deep can build resilient organizations and communities. The standard Silicon Valley orthodoxy is to scale up and fast, which arises often because of investor pressures. Many people do not question this orthodoxy, and yet it comes at a cost. There are numerous firms that sit in a graveyard of companies that scaled too fast and failed. I could sense the skepticism from many of the CEOs. Yet, one CEO and cofounder, Sriram Kannan, of Routematic agreed with me. I had the privilege to talk to him again and he was able to articulate so clearly how the scaling deep model works, partly by contrasting how scaling deep model of Routematic contrasts to the scaling up model of Uber. The fundamental principles of scaling deep are: 1. Grow organically from profits, not from investor cash 2. Master one market before opening up others 3. Focus on relationships, not transactions I think my biggest epiphany was that scaling deep does not mean slow growth or weak profits. Routematic has been able to achieve 8-10% month-over-month growth in revenues and has largely been profitable since it began offering its transportation services. Uber took almost 15 years to be profitable. I captured these ideas in the Forbes article I posted today, which was fun to write and taught me a lot. This is one of the many ideas I am exploring to see how systems thinking is encouraging a different way of thinking--where businesses can contribute to and benefit from stronger communities and a natural environment. As always, I welcome your reactions and provocations. Ivey Business School at Western University, Innovation North, Network for Business Sustainability (NBS), Kavitha Ramachandragowda, Ameya Uchil, Sebastien Guillaud, Thierry de Panafieu, #systemsthinking, #ScalingStrategy #SustainableGrowth #StartupStrategy #ProfitableGrowth #Entrepreneurship #Leadership #ImpactInvesting #SustainableTransportation https://lnkd.in/gM74UmYM

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I spoke with Christien Louviere of BDE Capital about his journey from a $330mm exit to becoming an independent sponsor. Christien shared excellent insights for folks looking to partner with business owners, rather than buy sellers out completely. Below are a few of the topics we covered: - Why he moved from “zero-to-one” startups to a buy-then-build strategy - How Christien's background shaped a focus on growth vs. cost-cutting - Why 20–40% rolled equity is central to his deal structures—and how it builds trust with sellers - Using scenario analysis with AI tools to evaluate management teams and uncover hidden key-person risks - How to identify when a $3–5M EBITDA company truly has a middle management layer—or is still founder-reliant For anyone investing in or buying small businesses, Christien’s approach provides a fresh lens on growth, alignment, and deal structuring. 🎥 Watch the full interview here → https://lnkd.in/ekfkaiej 🎧 Listen on Spotify: https://lnkd.in/e86Agx6V

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Camber Creek led the $3.7 million Seed round for TwinKnowledge, which is tackling an important problem in the built environment. Construction projects get delayed and rework is required because of discrepancies across construction documents, submittals, requests for information, design, and other plans. TwinKnowledge’s AI Agents absorb structured and unstructured project data, surfacing and preventing conflicts before the work begins. We’re excited about our partnership with CEO Ivan Panushev and his team. #construction #AEC #AI #technology https://ow.ly/mBYX50VtaVG

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I thought this was an interesting financing for both its scale and technique. General Catalyst launched their Customer Value Fund in which they “lend” growth capital to businesses that have found product-market fit, but their primary use of capital is to fund the burn caused by S&M spend (Sales & Marketing) or CAC (Customer Acquisition Cost). In Canada, ClearCo have been doing this for years with Ecommerce companies. According to GC’s website “With this strategy, GC pre-funds a company’s S&M budget. In return, GC is entitled only to the customer value created by that spend, and GC’s entitlement is capped at a fixed amount. After GC reaches that fixed amount, the remaining lifetime value of the customers is the company’s to keep forever. On the flipside, if the S&M spend does not pan out as expected, GC owns the downside – GC only gets paid if and when the company gets paid. The company never comes out of pocket to pay GC back.” The main advantage of this type of financing is to avoid the dilutive impact of financing. In this particular case, it might also appear to be an effective way to deal with the impairment in the value of the investment held by existing VC’s. The question is how is “customer value” calculated and what happens when there is no “customer value”. Is customer value simply the gross revenues generated from the S&M spend or is it the gross margin? What is the implicit cost of financing? What is the security in a downside scenario? https://lnkd.in/gC45QkPR

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