Jesse Middleton

Today, Two Chairs announces $72M of new funding to continue building a world where everyone has access to exceptional mental health care. Since late 2017, when Maveron led the Two Chairs Series A, the need for mental health services has grown considerably as our society has become lonelier and more isolated than ever. At the same time, our culture’s willingness to openly acknowledge these challenges is greater than ever. Sadly, the rapid growth of Two Chairs affirms the fact that our society is in desperate need of better mental health support. Two Chairs has built a business that believes clinical quality is the defining characteristic of success. Alex Katz has always emphasized the paramountcy of measurement-based clinical outcomes, which the team works tirelessly to achieve. In the process, Two Chairs has illustrated that embracing the ‘move fast and break things’ mentality doesn’t always work. Instead, Two Chairs opted for a different approach: they went slow to go fast. They built a proprietary algorithm that matches patients with the perfect therapist at the onset and hired a team of W2 clinicians oriented toward providing the highest quality care available. Even as the Two Chairs team has grown, their culture has remained small. This has enabled more intimate relationships within the team and between clients and clinicians. Reflecting on this milestone brings me back to the founding of Maveron and the values we hold dear. In 1998, my friend Howard Schultz and I founded Maveron to help entrepreneurs build companies that improve the lives of everyday people—their employees and their customers. There is perhaps no better example of this than Two Chairs. *** Thank you to TechCrunch's Marina Temkin, CFA for the great write-up. https://tcrn.ch/4aMt7yG

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We are so excited to announce our investment in Raechel Lambert, Bernard Kobos, and Ryan Lambert and their company, River Platform Company. River is a platform that empowers brands and influencers to build large-scale, in-person communities. To date, the platform has hosted over 2,000 events with 3,000 crowdsourced hosts and 55,000 attendees across more than 15 cities worldwide. We like to think of it as the operating system for community management. If the Catholic Church were founded today, it would use River to coordinate its global activities. No kidding. Jason Calacanis, the American internet entrepreneur and investor known for his All-In podcast with Chamath Palihapitiya, David O. Sacks, and David Friedberg, saw their potential early on. So did Balaji Srinivasan, Bryan Johnson, Tim Ferriss, and many others. We met the River team six months ago and have been incredibly impressed by their big-picture thinking, relentless hustle to connect with the right people and flawless execution. And as if that wasn’t enough, working with them is an absolute pleasure. These guys are a source of renewable energy. We’re proud to be part of this journey alongside wonderful co-investors like Blue Wire Capital, Blockwall, Solana Foundation, very early Ventures, and LAUNCH. Congratulations to the entire River team on this exciting milestone! We know firsthand that when things seem effortless, it’s because a tremendous amount of hard work went into making it happen. Want to join or host an IRL community event? Head over to getriver.io. #getriver #community #blockchainfounderscapital #startup #venturecapital #creatoreconomy

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Better Consumer Experiences in Everything... “We pride ourselves on being stridently anti-thematic, seeking out founders with bold, unexpected visions. From a black car dispatch service that became Uber to a Groupon-for-Korea idea that evolved into Coupang, a $30B ecommerce powerhouse, the best ideas often defy categories in their earliest days. We don’t know what category will be hot in 2025, but delightful consumer experiences are becoming a premium in an increasingly noisy world. People are demanding fewer, better experiences in everything from healthcare to content and media. For example, Suno transforms a few words into musical compositions made just for you. Whether mundane or magical, we plan to back ideas that turn the unexpected into essential experiences.” — Amanda Herson, General Partner, Founder Collective Thanks Maren Bannon and Forbes for a great topic with excellent curation ;) https://lnkd.in/ePgTvgvW

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Today marks a groundbreaking moment for BLCK VC and our fellow collaborators—Diversity VC, All Raise, 2Gether-International, SomosVC, StartOut, and VetsinTech—as we proudly announce the launch of the Diversity Data Alliance. This important alliance underscores our unwavering commitment to nurturing a venture capital and entrepreneurial ecosystem abundant in equity and inclusiveness. By standardizing and linking our data, we empower ourselves with the essential tools to track deeper trends that have, until now, eluded us to identify and fill funding gaps for historically excluded investors, founders, and operators. We can’t change what we do not measure, and now with the Diversity Data Alliance, we're now equipped to do both. Join us in this mission. Learn more and get involved: https://lnkd.in/eEZKdrac #DiversityDataAlliance #BLCKVC #VentureCapital #MeasureToChange

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I enjoyed going on Nick Telson-Sillett’s podcast, Pitch Deck by Forward Pursuit. Nick is a serial founder and investor (founded and exited DesignMyNight) so knows both sides of the table which always makes for an enriching chat. Some things we discussed: - The perceived power dynamic between VCs and founders can hinder productive conversations. - A compelling product demo can significantly influence investor interest. - Founders must focus on solving real customer problems to succeed. - Hiring standards are crucial for building a successful startup team. - Behavioural roadblocks can prevent the adoption of new solutions. - Validation from potential customers is key for pre-revenue startups. - The early-stage funding landscape has become more efficient and selective. - Pace of execution is a critical factor in attracting investment.

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I 💯agree with Oz Merchant on this topic. Some folks advise founders to pitch very selectively and 'pick your pitch' - you get one shot, choose it wisely? I'm 180 degrees opposite of that - be a promiscuous pitcher! - ABP - ALWAYS BE PITCHING. Because your pitch gets better with every no, take that feedback, learn, iterate. Right now it's taking 50-100 no's for Triangle co's to get funding, it's still tough out there, so get through the no's fast to get to a yes. Check out the event - also go see others pitch, it all helps you get better - pitching is like PMF - lots of iteration, tons of grinding to get through to the other side.

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Are you a #VC who needs #finance or #legal advice as fast as possible? Or are you someone who doesn’t already have an advisor working for you, and you need quick answers? This Axios article has introduced me to Decile Base by VC Lab: a free AI-powered chatbot tool that could potentially help VCs save money on third-party accountants or lawyers. To develop this tool, VC reached out to industry experts and converted over a thousand of those conversations into #OpenAI’s API, resulting in a chatbot that can cover a broad range of financial topics, like #tax advice. Decile Base is still in beta, and according to the CEO of VC Lab, Adeo Ressi, the techology is “not always right, but it is shockingly right.” To avoid hallucination, the chatbot will not provide answers to anything that’s outside of its field of knowledge. So, does Decile Base interest you? Have you used it before, and has it given you useful advice/information? I probably wouldn’t let go of your lawyers yet, but this is a handy tool to keep in mind in the future.

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The (Healthcare) Ground Beneath Our Feet… This year it is likely that over $10 billion will be invested in the digital health sector – a robust amount, no doubt, but inconsequential when compared to the amount of capital tied up in healthcare real estate assets, which is estimated to be $1.2 trillion by Jones Lang Lasalle. Of that amount, approximately $790 billion is in the hospital sector while the remaining $490 billion is in medical office assets. It is estimated that there are 48.6k facilities with 3.4 billion square feet of healthcare real estate, 42% of which are owned by REITs and another 33% held by other private investment vehicles. Much of the digital health investment is meant to make the physical healthcare infrastructure more productive: greater operating efficiencies, greater patient throughput, more relevant personalized care models with better outcomes. As the healthcare system is being pushed to be more distributed to lower cost sites of care, accelerated now by the rapid proliferation of automation and AI capabilities, the potential impact on healthcare infrastructure assets will be profound. Thoughts on what that might look like... https://lnkd.in/eTfAdUbS #digitalhealth Flare Capital Partners

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Congrats to the Revive team for the latest fundraise led by Equal Ventures, as well as the new brand! I’ve had the honor of working with Allison Lee (Founder/CEO) and team for almost six years as their first institutional investor. My gosh, it’s been an incredible–and at times harrowing–journey… ‘Revive’ is such an appropriate name for this company, on multiple fronts. First, it describes the core business well, where this platform helps large retail apparel brands to upcycle garments and deadstock into new products, thereby substantially reducing apparel waste. But it also accurately describes Allison Lee herself. Allison is one of the most resilient humans I’ve ever met, and she’s gone through hell and back to create this outstanding company. When we were first introduced to Allison in 2018 (thanks Bebe Kim for that intro!), Allison was a solo founder experimenting with mall kiosks that provided on-demand hemming services for retail apparel consumers. Over the years, Hemster (the name of the co back then) scaled up to become a substantial business, with her own warehouses and staff to handle hemming for top apparel brands throughout the US. But then the pandemic happened. Brand clients budgets collapsed, along with her business model, and Allison had to reduce her team down to just one person. Herself. This was a dark time. I remember reaching out and attempting to check in with her during a six-month period where she was at her loneliest as a founder. She pretty much locked herself in her apartment, mulling new directions for her company by herself. But she figured it out. In 2021, she saw that the consumer retail market was shifting as Gen Z was strengthening their purchasing power. This new generation of shoppers were more climate and sustainability conscious, and wanted to hold big brands’ feet to the fire for products that conformed to their values. Allison saw an opportunity to retool Hemster into a top platform to help facilitate upcycled products for apparel companies. And it worked! Allison breathed new life into her company and business has been growing quickly ever since. Her business’ thesis is even stronger and bigger than the one she initially launched with. Beyond her being a skilled founder and operator, Allison is also a fantastic human being. She is relentless and un-killable as a founder. And also so warm, kind, and present as a friend. I’m grateful to call her a friend today, as well as a role model. Allison’s journey is still in the early days with Revive, and no doubt she is going to build something that has a huge impact on this world. Hustle Fund is nothing but grateful that she said YES to us, and allowed us to be part of this amazing and inspiring journey. Congrats again, Allison and team!

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What do you do when a radical new technology puts your main product right in the crosshairs of disruption? Listen to David Okuniev — co-founder of Typeform | Ask awesomely — discuss the challenges of innovation within existing structures. David shared a game-changing insight: Radical innovation is really, really difficult to do inside your own product. He emphasized the need to break free from the constraints of familiarity and embrace change from outside the box. Henrik Werdelin and I have both seen our fair share of this in our respective careers. What struck us most was how David leveraged structure to overcome the innovator’s dilemma. By creating a culture of experimentation and providing space for bold ideas, he propelled Typeform beyond incremental improvements. What other hacks have you seen or employed to help your organization overcome the innovator’s dilemma? Share your stories below! 👇 And if you want to dive deeper into our conversation, click the link in the comments to catch the full podcast episode!

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Great time on the Embracing Erosion podcast w/Devon O'Rourke! We talked about: 🚀 How to scale a company from concept to 9-figure exit 🔄 How to break away from the traditional consulting model and apply product approaches ⏩ Why it’s important to iterate quickly and often with messaging 💸📈What signals are important to pay attention to when investing in startups and much more!

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Rolling into another day of the Primary Summit. Hit me up if we should connect onsite. Kudos to the Primary Ventures team so far, as yesterday’s Pre-Seed Summit was on point. Mar Hershenson, Benjamin Sun, Chris Douvos, Zach Weinberg, and Graham Pingree all dropping helpful nuggets for fund managers. Some paraphrased highlights: - Chris Douvos (AHOY Capital) - Most fund decks are terrible. Start with your people (not your strategy) and know you have about 6 slides of his attention. - Zach Weinberg (Curie.Bio ) - beleives SF’s AI talent is a significant advantage over NY, wouldn’t build AI in NY. Also questions if VC exits can keep up with VC expansion (generally hilarious and smart Twitter follow) - Mar Hershenson (Pear VC) - VC is so much more competitive now. It’s not enough to be an ex-founder with a great network and domain expertise. Have a better “why you are different” or do something else! - Benjamin Sun (Primary Venture Partners)- still sees arbitrage in going long NY venture (vs. SF). Do the work to keep various influential networking nodes aware of what you’re doing and how you think.

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🚀 Calling all fundraising Boston Metro B2B tech startups! 🚀 Are you currently fundraising and ready to pitch in front of Boston's top angel investors and early-stage fund managers? On November 19th, Venture Lane | Startup Hub is hosting our exclusive Pitch Night 👉 - a rare opportunity for Boston Metro’s early-stage B2B tech founders to present their investor pitch live and connect directly with key decision-makers in the local investment community. We’re on a mission to showcase the next wave of standout B2B tech companies from Boston. If you're ready to elevate your fundraising efforts and make meaningful connections, don't miss this opportunity. ⏰ Apply by October 22nd to secure your spot! 📲 Find the application link in the comments below. #B2BTech #Startups #Fundraising #BostonStartups #PitchNight #VentureLaneStudio

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I just wrapped up a panel with the Marketing Leadership affinity group within the How Women Invest community with my hero Auntie Nancy Hayes, aka the Yoda of board membership, angel investing, and general badassery. We talked about different ways to serve on boards, a role in which experienced Marketers seem to be often underrepresented. Why? If I had to guess, I'd say: 1 - Most heads of marketing are women 2 - marketing is undervalued, especially under sales/revenue experience 3—Compound the first two with the messages you tell yourself about your own worthiness, and suddenly, you're a great marketer for everyone else but yourself. ___________ For those who are interested in getting closer or into the board room, there are so many ways to start/get experience: 1—Board Observer (one of my current board roles)—you represent the investor but have no votes. It is unpaid, but/and hugely essential to act as a bridge of visibility and communication between the fund you've invested with and the company in which the fund has invested. My role brings value to both sides with much less bias than the other VC board seats. 2—Corporate board director—There is much governance but not much influence on the product, as the company usually has big enough teams for that. There is a lot of hiring/firing CEOs (read: drama), which can still be fun, especially for those fresh-popcorn-in-my-bag swag kinda folks (both grossly generalizing and way understating this role's fiduciary importance, but you get the idea). 3—Independent board director—this is another of my favorite places to sit. It is much like the Board observer role but with voting rights and equity (although not always, as these terms are negotiated and influenced by the shareholding board seats). You are NOT representing a VC fund (typically), but you might have subject matter expertise in the product or are a generalist boss gal like myself and bring a sense of neutrality and balance to the board. 4—Advisor. Advisors are similar to IBD in terms of influence and type of advice but are not part of the board or its meetings. This role is usually paid in some combination of equity and cash. It's another of my faves. (Are you seeing the trend here?) We have not even touched non-profit boards (where I got my start and am currently sitting on my sixth), but we will save it for next time as it's a whole 'nother Oprah. If you want to learn more, How Women Lead is hosting its 5th annual #getonboard week, starting October 21. Hybrid virtual and in-person. Check it out: https://lnkd.in/diizwv8j #womeninleadership #boardofdirectors #howwomenlead #governance #boarddiversity #corporategovernance #boardservice #businessleadership #leadership Julie Candelon Susan Greenwood Schroeder Mikayla Ludwig

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Our revamped newsletter, The Angle by Angular Ventures, officially launched today! We hope this new format will make it easier to read, share, and subscribe. Back to it, in this week's column, Gil Dibner covered the spirit of risk-taking that inspired Angular to venture into unusual spaces. While, of course, we invest in AI and SaaS, as of late, we have been investing in more and more contrarian spaces - from quantum, to spacetech, to energy, etc. in search of the supposedly impossible - the truly contrarian. Read the full column via the link.

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Are you an emerging manager in VC who wants two free coaching sessions--and an invite to a best practices seminar for fund investors? With Sydecar's help, I'm giving away three two-session packages. Details below! A little less than a year ago, I wrote a blog post (https://lnkd.in/eRi6CueH) asking why more emerging VCs didn't seek out coaching. I got flooded with everyone from new associates to partner track principals at top-tier names to GPs of emerging funds. It's been extremely rewarding to leverage my twenty years of experience across Union Square Ventures, First Round Capital and Brooklyn Bridge Ventures to help the next generation of investors. My coaching basically comes down to helping investors focus and Sydecar shares this goal. Their platform reliably handles back-office operations, automating banking, compliance, contracts, tax, and reporting so that their customers can focus on making deals and building relationships. If you fill out the form below by next Friday, June 21st, you'll be entered in a drawing to win one of three free two-session VC coaching packages from me and also invited to a best practices seminar for emerging managers. https://lnkd.in/egUh2V-J

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Lately, I've gotten a few great questions about how venture-builders (#VentureStudios in particular) go about recruiting great #founders. For investors looking at a studio, this is a critical diligence factor. For operators, it's make or break for each venture. And for the founders themselves, the expectations might be very different than they might think if they aren't familiar with the studio model. Here's how I think about it. The job is different when you run a company in a studio - there should be less range and greater intensity of focus. Job one is hone in on product-market fit and establish solid unit economics. While the studio supports GTM strategies, recruiting, and fundraising, founders shape the pace and prove out the concept for the companies. So, what kinds of founders thrive in that type of environment? Here are the attributes I get excited about: 🏃‍♀️ nimble, ❓ curious, 🧠 decisive, and 🤝 collaborative. While targets might be clear, the path and process are likely to shift. Making sense of that and moving fast is mission critical. What else, though? I'd love to hear from others who have different takes than mine!

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After the first deep dive discussion w/ founders I often hear a comment "I wish I had heard about this alternative [to all-in must-become-a-unicorn] way to build a startup earlier as I have wasted years in pursuing the wrong thing". Our mission is that no founder would ever need to say that again as it is such a waste. Us preaching the gospel 1:1 just doesn't scale, hence we use mass media to multiply our efforts - that's how Gorillacast came to be. The 1st episode is out, featuring yours truly. "How can you know what food you like unless you taste everything" said a chef. How can founders make informed choices about the best strategy for them to follow unless they know of all alternatives? This might not be of interest to you but pls spread the word so that the founders who should hear it can find it. I have a dream!

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