Sunil Rajasekar

Next one up, Flagler Health! In an attempt to demystify some of the non-obvious elements we found when we first met the founders of our fastest growing portfolio companies at 186 Ventures, here is the third edition of the "idiosyncratic phenomenon". This highlight will be on Albert Katz, Leon Anijar, and Will Hu and their journey building Flagler Health to bring unprecedented AI enabled patient care to the world of musculoskeletal (MsK) providers. As the healthcare industry shifts to a value based care paradigm, there will be increased pressure on the entire industry to ensure patient outcomes improve, all the while helping providers generate more revenue / become more cost efficient. Since we co-led their March, 2024 seed round with Streamlined, the company has rolled out some of their newest remote therapeutic and chronic condition management features to many patients and providers alike, experiencing high revenue growth in such a short period of time. The company continues to face unmet customer demand as it continues to scale its expansion into 2025. https://lnkd.in/exesTcmC

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In vertical SaaS, the very best companies landed with a product solving a specific, burning pain point that horizontal solutions solved badly and then became broad product suites over time (ServiceTitan, Veeva Systems, Doximity, etc). My partner Gordon Ritter calls this “layering the cake”. In vertical AI, the landing wedges are much more brittle. While the painpoints they solve are very real (and often unaddressable by SaaS alone), they’re also much more likely to commodotize in the near term as the tech advances. 👀 Therefore, the need to layer the cake in vertical AI is much more urgent than in vertical SaaS. 👀 The best vertical AI CEOs not only recognize the dynamic, but talk about it openly. Helps those around them keep up the speed of innovation and their eyes on the bigger prize.

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The payment processing space is in for a rude awakening. There is a complete, lack of transparency across the entire industry. From the networks, to the processors, to the sponsor banks. To be honest, it's disgusting. We have been working with a handful of processors who are more forward-thinking and trying to streamline the fees and market. However, it's amazing how opaque the market really is. We just ran an assessment on all of our processing fees down to the penny, from the network fees through processing fees. Here is a list of all of our network fees 🤯🤯🤯🤯🤯🤯🤯🤯 Send help.

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As we explore a seed round of VC funding for Avnir, a mentor has driven into me to "interview them as much as they'll do their due diligence on you!" When I consider professional etiquette important to me (and probably every serious founder), I am reminded of what I've coached hundreds of executives on over the past two decades: "Your culture is a culmination of behaviors you're willing to tolerate!" So, here is a Top 10 List of Professional Etiquette crucial to long-term strategic relationships between VCs and founders: 1️⃣ Respect for Time—Punctuality, Efficient Communication, and Timely Feedforward are demonstrated and genuinely felt. We would both rather me invest time in building the business. 2️⃣ Transparency—Clear Expectations, Honest Feedforward, and Disclosures on conflicts of interest or resource limitations save everyone unnecessarily wasted cycles! 3️⃣ Professionalism—Politeness, Confidentiality, and Objective Evaluation allow courteous interactions, respect for proprietary information, and avoiding bias in evaluating the founder's meritocracy. 4️⃣ Empathy—Understanding the Journey and Constructive Dialogue acknowledge the uphill battle founders face while avoiding unnecessary criticism and providing supportive guidance, demonstrating a genuine interest in their vision. 5️⃣ Integrity—Fair Terms, Follow Through, and Avoiding Overpromising honor commitments during discussions, and create realistic expectations from the relationship. 6️⃣ Co-Creation—Value-adding Mindset and Team Player Attitude accelerate the founder's ability to gain traction and position the VC relationship as transformational vs. simply transactional. 7️⃣ Humility—Avoiding Arrogance, Condescension, and Open-Mindedness acknowledges that both parties have unique expertise to add and enhance the receptivity to unconventional ideas, approaches, and perspectives. 8️⃣ Listening Louder—Present, Engaged, and Clarity of Intent eliminates distractions, brings out what's not being said, and jointly crafts better questions to help uncover the unknown and the undiscovered. 9️⃣ Encouraging—Supportive Communication, Positive Reinforcement, and Inspiration help celebrate small wins and key milestone achievements. It's ideal to light a fire within the relationship rather than under anyone, which seldom lasts! 🔟 Playing the Long Game—Relationship Nurturing and Post-Investment Care establishes the runway for a lasting partnership rather than simply pitching a deck and closing a deal. After the investment decision, sustaining the relationship will determine the partnership's long-term perspective. Jason M. Lemkin, Peter Bell, Cassie Young, and Ed Sim - you exemplify world-class in the relationships you build with your founders. Did I miss anything? #VCFounderRelationship #AlignedExpectations #RelationshipsMatterMoreThanEver

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"Some Credit Unions are a generation away from being obsolete." Woah, ... that was a surprising statement. Thanks to our good friend Mark Chandler, we got to spend a wonderful night on the water in San Diego as part of the Origence's LendingTech conference. Tom Orman was sharing his thoughts on Credit Union and FinTech partnerships. Tom explained that over 25+ years in the Credit Union space, things have accelerated to change rapidly, especially post-Covid. For an outsider to the Credit Union industry like me, it's easy to assume that all Credit Unions are the same. That's far from true as I've learned over the last 4+ years: There is a wide spectrum of Credit Unions: super innovative ones and then others who prefer doing things "the way they've always done it." A lot of what Tom said was in line with our observations summarized in the attached thought leadership piece. Key Points from Tom and my conversation that align with what we've learned about the industry: 🚀 Innovation Spectrum: Credit Unions range from highly innovative to those sticking to traditional methods. 📉 Digital Transformation Needs: Credit Unions must embrace digital transformation to stay relevant and competitive. 🔄 Change Management: Successful change requires top-down support and a willingness to break away from the "we've always done it this way" mentality. 📱 Member Experience: Enhancing digital onboarding and creating a seamless omnichannel experience is crucial. 🏦 Financial Health: Effective digital strategies can significantly reduce loan origination and member acquisition costs. 📈 Growth Goals: Ambitious Credit Unions with strong growth goals are more likely to embrace and benefit from technology. 🌟 Cross-Selling Opportunities: Credit Unions should leverage technology to cross-sell products and deepen member relationships. 🌍 Industry Challenges: Credit Unions face unique challenges, such as maintaining member loyalty in a digital age dominated by direct-to-consumer FinTech innovations. If I missed something, please leave a comment or ping me. Ending the week with a lot of gratitude for everything the Credit Union has given us and enthusiastic, excited and motivated to give back tenfold! None of what Clutch is doing would be possible without generous folks like Tom Orman, who share their insights and guide us through how to prioritize our technology efforts. Thank you, Tom, and everyone else who contributes to this ongoing journey of transforming the Credit Union industry. If you want to read on, take a look at the following Whitepaper: https://lnkd.in/d7NSjr2t

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In the latest Hooswhere Podcast episode, we are joined by Jen Finn CEO and co-founder of HIO. Jen shares her inspiring journey from consulting and her role at Capital One to leading a tech startup focused on transforming the multifamily housing experience through conversational AI. This episode dives deep into the evolution of real estate, the challenges and opportunities in the multifamily market, and the importance of mentorship and alumni networks. Jen also offers valuable insights into angel investing and scaling innovative solutions. If you’re passionate about technology, real estate, or entrepreneurship, don’t miss this conversation. Watch the full episode here: https://lnkd.in/eFtJTPRS What’s your biggest takeaway from Jen’s journey? Let us know in the comments. #HooswherePodcast #UVAAlumni #Entrepreneurship #RealEstateInnovation #AngelInvesting

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I had an absolute blast with Michel Gagnon and the Stun and Awe crew - THANKS again for having me... Sneak peek of the substance below: > Micro SaaS companies can be just as safe and stable as larger businesses, offering lower valuations and less competition from institutional players. > Founder-product fit is crucial, as founders solving their own problems often create useful products with great retention. > Founder burnout can be a buying signal, indicating a solid business with a founder ready to move on. > The first 90 days post-acquisition should focus on visibility, documentation, transition, and validating diligence assumptions before pursuing growth. > Building transparently and maintaining open communication with users post-acquisition helps preserve the human element and avoid the pitfall of going silent. > Simplicity equals mastery - if it takes a complex explanation to justify an acquisition, you probably don't fully understand the business. > Establishing reasonable incremental growth goals based on baseline performance (systems over goals) is more effective than setting arbitrary targets. > Fostering a culture of care and respect enables honest feedback and allows teams to move faster through a shared commitment to truth-seeking.

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Six ideas of Dileep Thazhmon, founder and CEO at $2.1B fintech Jeeves, that stuck with me after our The J Curve conversation 👇🏻 1️⃣ In this market, surviving is thriving. The companies that make it through tough times will emerge stronger. 2️⃣ Good people like to work on hard problems. The best investors are drawn to supporting these challenges. 3️⃣ Your most valuable resource is time. Solve for the steepest learning curve because you won’t get that time back. 4️⃣ If you see a window of opportunity, move fast—because if you don't, someone else will. 5️⃣Entrepreneurship is about change—embrace it as a creation event, not something to fear. 6️⃣Hiring isn’t just about filling roles—it’s about finding relentless individuals who push the whole team forward. Watch / listen to our full interview by tuning into our channels on Youtube, Spotify and Apple 🔗👇🏻 #entrepreneurship #leadership #venturecapital #startup #foundermindset #fintech

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In his latest piece, Paul Graham dives into a thought-provoking realization sparked by Brian Chesky's memorable talk at a recent YC event: **what if the conventional wisdom on scaling companies is fundamentally flawed for founders?** Graham dissects why advice that works for professional managers often fails founders, leading to disastrous results. He introduces the concept of "Founder Mode" — a distinct approach to running a company that clashes with traditional management practices. Graham argues that embracing this mode could be the key to unlocking greater success for startups, potentially revolutionizing how founders scale their companies. Made me think. https://lnkd.in/exHmEE5M

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🔑 The Power of a Written Exercise in Interviewing Revenue Leaders 📝 Hiring the right revenue leader can make or break an organization. As we search for smart folks to drive our revenue growth at Vanta, one approach has consistently proven to be a game-changer: the written exercise. 🔍 Why a Written Exercise? Clarity of Thought: A well designed exercise reveals a candidate's ability to articulate complex ideas clearly and concisely. This skill is vital for revenue leaders who must communicate strategies across diverse teams and stakeholders. Strategic Insight: Through real-world scenarios, candidates demonstrate their strategic thinking and problem-solving abilities. This helps us gauge their approach to challenges and opportunities unique to our business. Analytical Prowess: Written exercises allow candidates to showcase their analytical skills. By dissecting data and presenting actionable insights, we can see how they drive decisions that lead to growth. Cultural Fit: How a candidate approaches a written task can also give us a glimpse into their work ethic, attention to detail, and alignment with our company values and culture. Elliot Goldwater has really nailed this practice, and it's incredible how much the exercise can swing a process towards or away from a candidate. 👥 Have you implemented written exercises in your hiring process? What has been your experience? #RevenueGrowth #Leadership #HiringTrends #Interviewing #TalentAcquisition #Strategy

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How do you validate a business model without investing $$$ in tech? 🧙‍♂️ Ravi Kurani did just that with his earliest MVP for Sutro By concierging a ✨Wizard of Oz✨ type of experience, he intentionally ran an "inefficient" process to see if customers would pay—and they were hooked. People didn’t want to give back the *mock* version! Sometimes, the best insights come from scrappy starts, and early feedback can make all the difference. Full interview and PMF strategy template inspired by Sutro + Superhuman in the latest newsletter -- link in the comments!

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"The ice is beginning to melt on what was a wintry period" - Laura Bock, partner at QED Investors ☃ In Q1 2024, venture capital funding for payments startups was 85% down year on year, marking a six-year low. This sharp decline reflects a broader trend of decreased investments across the fintech sector. 🙁 HOWEVER...... 👇 Surely this will soon change with favourable structural and technological tailwinds opening up exciting opportunities around the topics of account to account payments and payment authentication. PSD3 is going to be a turboboost for open banking kicking off a whole new wave of innovation and value-added services. 🚀 https://lnkd.in/d_c_At8V So place your bets if you dare. What will be the hot topic in the payments that will kick off the next VC bull run in the space? 🤷‍♂️ #VentureCapital #PaymentsIndustry #Fintech #Innovation #StartupGrowth #A2A #Account2Account #Payments #psd2 #psd3 #fraudprevention

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Monetizing payments has traditionally been either easy or lucrative for software providers, but not both. Now, with the rise of embedded payments, that's no longer the case. While not all embedded payments solutions are created equal, finding the right partner can help you achieve long-term profitability and success. Our Head of Product for ISV Embedded Experiences and Partner Revenue Acceleration, Steven Madow, wrote an article for NMI that explores why so many software platforms are choosing to partner with providers like NMI for payments. He discusses the benefits of the partner-enabled model, including: -Greater choice and flexibility -Enhanced user experiences -Built-in expertise and support -More lucrative revenue potential See what else Steven has to say here: https://bit.ly/3ybkob5

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My predictions for what 2025 will look like for the world of startups 1/ Funding toward legacy vertical SaaS businesses will hit an all time high in 2025. 2/ Flight to SF: SF will be the place as a preseed & seed founder to raise their first rounds. The emerging founders will pop in in SF first before making their ways to NYC and beyond. 3/ Year of Exits: We'll see a lot of the companies that couldn't exit in 2022-2024 start to exit this year through IPO, M&A and more. Will add much liquidity towards the VC market and drive LP diversification versus in 2024 where $35B of the $72B raised towards VC firms went to the top 9 venture funds in the world. 4/ Early stage fintech makes a comeback: The peak for early stage fintech was 2022 with $4.1B raised across 970 deals. 2024 early stage fintech numbers fell to 5 year lows with only $1.9B raised across 505 angel, preseed and seed deals. Seeing some improvements in funding numbers from quarter lowers which was Q2 2024 and some improvement in Q4 2024. Macro trends, AI, and some late stage funding for later fintech cos gives me an impression early stage fintech will rebound next year. 5/ RTO is coming back: The best startups will no longer be distributed but will return to the office in 2025. We'll see an increasing amount of startups, especially the early stage ones, emphasize in person work and hires. 6/ Biohacking the supermarket: Interest in health and longevity for consumers and the advancement of AI are long to lead to more demand for personalized food plans built for each individual person. 7/ Built for you: media and everything we consume on the internet will become for you. Think an extension of the for you page on Tik Tok but for everything else you consume, shop and watch. It won't be long until media becomes personalized to you and I and your favorite influencer is actually AI. 8/ Digital Twin Simulations: Someone will build out your digital AI twin for decision making. From testing career changes to planning relationships, these virtual replicas could provide insights into life’s "what-ifs. 9/ AI buyers: Just like with the rise in SDRs, we'll soon see a company test our buying with AI. Take product features, demos, pricing and more into account and AI will optimize to buy the right vendor stack for a founder based on exactly what they need.

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New Episode: Let's take a look into the nuts and bolts of VC and what it takes to be an effective manager... I chat with Marlon C. Nichols (Managing General Partner, MaC Venture Capital), a Kauffman Fellows BoD member, and one of the Pitchbook's "25 VCs to Watch". (link below) We discuss topics such as: - Marlon's journey from early operator in enterprise software to VC founder - Venture capital as a path to diversity and strategic engagement - Mac Ventures investment thesis and strategies - Advice for new GPs - Strategies for First-Time fund managers targeting LPs - Strategies for startups targeting successful exits - Evaluating seed stage investments - Venture capital’s shift to sustainable investment strategies - The impact of AI on business Apple Podcasts: https://lnkd.in/g-JVnxFQ Spotify: https://lnkd.in/gWeqVkqX

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How companies purchase software is rapidly evolving, with cloud marketplaces expected to reach $100B in 2026, up from $15B in 2023. Simply put, if you are building and selling cloud software today, it's imperative that you can sell through a cloud marketplace. The journey, however, can be a little confusing, and management can be even harder. With 3x growth last year and 3/4th of our business now flowing through a cloud marketplace, CloudZero switched to Clazar earlier this year to handle our rapid growth, and I couldn't be more thrilled. Trunal B. and Aayush Bahuguna have a big vision for how cloud marketplaces will evolve and how software will be bought and sold in the future. No matter where you are on your journey, learning from them what's coming next is worth your time.

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There are more than 50M gig-workers in LatAm alone. We are talking about the backbone of the new economy: ride-share drivers, last-mile delivery workers, cleaning service providers, handymen, massage therapists, nurses, and many others. Unfortunately, over 75% of them live paycheck to paycheck. Olé tackles the root of the problem by working shoulder to shoulder with businesses and giving hard-working Latinos access to their earnings on-demand, helping them avoid predatory loans. Olé's team is passionate about solving real world problems. If this resonates with you, let's chat. "The future of work is on-demand, and payments will also be 24/7/365/On-demand" Shout-out to Andrés Cano, Daniel Ospina, & the Pygma team for all the support. #LongLatAm #LongFinTech

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Ascend just released this new interview about why I love investing in Seattle/Pacific Northwest (PNW) startups at Ubiquity Ventures. Ascend is the most active pre-seed investor in the Pacific Northwest (Seattle, Portland, and more) and is run by Kirby Winfield. Thanks to Ascend's Nate Bek for the interview! Check it out the full interview: https://lnkd.in/giU2Wy3V A few snippets of what I said: ⭐️ On investing in Seattle (vs the Bay Area) "Companies like Auth0, Esper, Remitly, and others have demonstrated that they can start, grow, and thrive in Seattle. This is thanks to the continuous growth of hometown giants like Amazon and Microsoft, whose employees might outgrow the cultures at those companies." ⭐️ Why I fell in love with VC "First is about following new trends, nerding out on technologies, and getting inspired by new ideas .. resonates with the nerd engineer and the 5-year-old in me that used to love reading about new technologies ... [Next is] the innards of how companies are run, being in those pivotal meetings and discussions that change the direction of a company. These hard conversations about pivots, understanding metrics, and trying to separate the storytelling around startups from internal operations. That was the meat of building an exciting startup, which is quite different from just nerding out on cool new technologies. " And thank you to all the Pacific Northwest startups I've been privileged to invest in and work with: Eugenio P. and Jon Gelsey at Auth0 by Okta, Yadhu Gopalan at Esper, Fredrik Rydén at Olis Robotics, Claire Watts at ThruWave Inc., Adam Schoenfeld & Aviel Ginzburg at Simply Measured, Milkana Brace at Jargon, Yuriy Bulygin & Alex Bazhaniuk at Eclypsium, Inc. #seattle #seattletech #pacificnorthwest #pnwtech #portland

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Curious about how we spot the most unobvious winners at seed? It’s simple - we invest in those we’d never want to bet against. In 2017 slice was a scrappy fintech financing smartphones for college students. Today, it’s set to become India’s first true digital bank, catering to the needs of India’s Gen Z. With this merger, Slice is poised to simplify digital banking for a billion Indians, establishing a new gold standard of customer-focused banking.

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