Mary Chestak

How Etsy built a global marketplace one craft fair at a time... Rob Kalin is a maker of things. Bed frames, chairs, cobb ovens for bread—even his own underwear. After graduating college in 2004, he fell in love with carpentry, offering his amateur skills to friends around Brooklyn. In 2005, Kalin crossed paths with Jean Railla—founder of Get Crafty, an arts and crafts forum. Railla needed a new website and asked him to build it. Kalin said yes. During the build, a question loomed large: Where do artists sell their creations? Kalin pitched his idea for an arts and crafts marketplace to Railla, who resonated with the vision but wanted to keep her site focused on community discussion. Armed with the idea, Kalin and his artist friends decided to create their own marketplace for makers and craftsmen. He called it Etsy. On June 18th, 2005, Etsy greeted the internet. The first product? A flamingo print zip pouch for $8. But Kalin and his team didn’t stop with the flamingo. They attended every arts and crafts fair, flea market and vintage sale across the U.S. and Canada. They bought artists lunch, handed out “craft show kits,” and shared handmade Etsy promos. “These were artists and crafters influential in the handmade world,” Kalin said. “We knew if they set up shop on Etsy, and were successful, others would follow.” And follow they did. In year one, Etsy had 9k sellers, 22k buyers, and over $1 million in revenue. Two years later: 450k sellers, $26 million in annual sales, and $3 million in VC funding. Today, Etsy is the powerhouse niche marketplace with 96 million buyers, 8.6 million sellers and over $2 billion in annual revenue. None of that would’ve happened if they hadn’t stepped away from the screens and into the real world. The lesson? Success isn’t built from behind a desk. Show up, connect and the rest will follow.

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TryNow.com Weekly Update ⚡ • Hosted a great dinner for 20+ brand operators in NYC last night with Eli Weiss. Thanks for coming out Jeff Hansen, Alice Kim, Vanessa Alvarez, Katrina Caraboolad, Ian Laya, Loris Spadaccini, Arjan Singh, Timothy W. Schifter, Laurie Mucciolo, Madeline Placik, Kyle Goldman, Nicole (Nico) ✨ S., John Wong, Michael De Santis, Adrian Aidid and many more. • If you've been following along, you know that we made a big shift towards product-led engineering towards the end of Q1. This means that as a company we spend more time describing problems rather than prescribing solutions (shout out to Steve Davis at TryNow for this sound articulation) and empower engineering to fully own the solution. By defining the problem in detail, solutions can more naturally flow out of that work. Shifts like this are by no means immediate, and this week capped off a month of very strong product-led engineering. Keep an eye out for improvements to self-service onboarding, enhancements to TryNow Insights Dashboard, and some impactful improvements to our automated capture process. A few companies that inspired this cultural shift towards product-led engineering are PostHog and Ramp, two very different companies that share a product development velocity that we admire. • Incredible week in NYC with Ian Schneider, Director of GTM at TryNow. At dinner last night, a prospective customer came up to us and shared praise for our sales process. He mentioned that we don't "sell", we don't apply any pressure, and we're the most customer-centric vendor he knows. Now, I know there's a lot of improvements we can and should make to our GTM motion to ensure we're always putting the customer at the center. But we're on our way. Keep it up, Ian 🤜 #TryBeforeYouBuy #TryNewThings #Shopify

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Awesome new product from Forum Ventures portco Fireflies.ai. If you're not using an AI notetaker for your meetings yet, definitely try them out. With this new feature, you get an AI Chief of Staff who knows what's happening across your org, captures important information from different conversations, and organizes it all into one place.

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Now that I’m a pre-seed founder with no income, I’ve downgraded my commute from Uber to the MTA Bus. It’s humbling but also taught me a lot so I decided to share the biggest lessons I’ve learned from eating this humble pie. 🌟**What Taking the Bus in NYC Taught Me About Enterprise Sales**🌟 Ah, the New York City bus. A beacon of efficiency and comfort. No delays, always on time, and the perfect place to learn about enterprise sales! 🚌💼 1. **Patience is a Virtue:** Just like waiting for that elusive client decision, waiting for the bus teaches you that time is just a construct. Why rush when you can enjoy the scenic view of the same block for 20 minutes? ⏳ 2. **Building Relationships:** Every bus ride is a networking opportunity. Whether it’s the person sharing their life story with you or the one falling asleep on your shoulder, these encounters are invaluable for honing your people skills. 🤝 3. **Handling Rejection:** When the bus doors close right in your face, it’s just like losing a deal you were certain you’d win. Brush it off, wait for the next one, and hope for a better outcome. 🚪❌ 4. **Strategic Planning:** Navigating the bus system requires a level of strategic thinking akin to planning a multi-million dollar sales pitch. One wrong move and you end up in Staten Island. 🗺️ 5. **Optimism:** The sheer optimism of believing the bus will come on time, despite all evidence to the contrary, mirrors the unwavering belief in closing that impossible deal. 🌈 So next time you're frustrated with your sales pipeline, just hop on a bus. It's basically a masterclass in enterprise sales. 🚍📈 #SalesLessons #EnterpriseSales #NYCBus #LinkedInInfluencer #TotallySeriousPost

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Last night at Soho House, a couple of founders cornered me.  "We’re building the next SpaceX," they said. "But we don’t have a CTO yet." I stared at them for a solid five seconds. Then texted my dealer: "I need to double. This industry is killing me."  Here’s a stat for your pitch deck: SpaceX added $100B in value in 30 days. That’s $138M per hour. And they didn’t do it with founders who think technical talent is optional.  At Wally Capital, we’ve seen it all founders who think they can outsource rockets on Upwork, founders who think technical co-founder means their mate who did coding once. 1. Hire a CTO. Not your buddy from uni who dabbled in Python. Someone who can actually build things that leave the ground.  2. Stop pitching SpaceX as your role model. You’re not SpaceX. You’re barely a pitch deck.  Until then, you’re building my next case study on how not to raise. ____________ ⭕️ Get it? Want more? Well, lucky for you, there’s more where that came from. https://shorturl.at/1oiJR #startup #founder #tech #vc #valuation #ai #funding #investment #space

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It’s NY Tech week and my new favorite thing is teaching underrepresented founders how to talk back to investors. So many of them ask me for help fundraising, and I get it. I may not always think of myself as an expert, since I’m lucky enough to surround myself with people who are much more experienced at it than I am. But we did do it successfully once, raising more than $3M along the way with little more than a deck, a dream, and an incredible founding team. Of course, we’re all aware that this success puts us in the teeny tiny cohort of startups who raise without a traditional-looking founding team. So what’s the common theme in my advice to non-traditional founders at the early stage? Push back. It’s easy to get intimidated by investors. They’re smart, aggressive, and ask really hard questions. It can be hard to remember that YOU are the expert on your market. They are generalists. Even if they have strong opinions on your market, it’s OK to tell them when you think they’re wrong. In fact, if you have the conviction and confidence (plus evidence to back it up), disagreeing with your prospective investors can even be seen as an advantage. When a VC asks you a question at the pre-seed stage about your path to $100M in ARR, it’s OK to say “dude, we’re a pre-seed company. I know what our path is to get to a million, and we will have a lot to figure out after that.” Now, this only works if you have a track record that can support your confidence. Or if you don’t know the answer, but you DO know HOW you’re going to figure it out, talk about the path from experimentation to scalability. It’s better than making up a bunch of stuff that you’ll probably throw out eventually, and VCs will respect your focus and defense of your precious little time. Plus, they can usually tell if your confidence is lacking in your answer, anyway. This investor market is a tricky one, but never forget that they (investors) need you (founders) just as much as you need them. And hey, if you’re an up and coming female or underrepresented founder, and you need some help (or just a pep talk) I’d love to help. Happy Tech Week everyone!!

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"This blog delves into the key considerations when looking for synergies between two businesses during an M&A deal, focusing on technology, R&D resources, and corporate IT. We will explore how these synergies can be evaluated and maximized to ensure a successful integration and value creation."

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Unsolicited feedback is the biggest gift you can get as a founder. But here’s the trap many early-stage founders fall into: The moment someone shares feedback, they immediately jump into defense mode—justifying their thought process, decisions, or product vision. Here’s the truth: feedback, resistance, and even challenges are invaluable because they expose you to perspectives you may not have considered. The key isn’t to justify—it’s to listen, observe, and dig deeper. 👉 Here’s a perspective to think about: A friend recently shared how they felt humiliated after being insulted by a colleague in public. It’s a tough situation, no doubt. But it was also their first experience handling such a moment. If approached with the right mindset, this moment becomes a gift — a chance to learn and be better prepared next time. 👉 The same applies to feedback: Someone giving you feedback means they see potential—they care enough to want you to improve. But not everyone is articulate in their feedback delivery. Sometimes, frustration or disappointment is just a poorly communicated desire for something better. The best thing you can do? • Listen verbatim. Resist the urge to customize your response. • Stay curious. Ask questions. Understand the underlying decision-making process behind their feedback. • And most importantly, use their input as a tool for root cause analysis (RCA) rather than rushing to defend. I’m sharing this because I’ve made this mistake myself. As a founder, our natural instinct is to defend our work—it’s personal. But the sooner we let go of this mindset, the faster our offering can improve. So, here’s my advice: Feedback isn’t an attack; it’s an opportunity. Wishing all of us a lot of feedback this week ❤️ 😅 #Feedback #FoundersMindset #StartupLife #Growth #Curiosity

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The next generation of NYC investors are already making their mark. Under 30, bold, and already making moves, they’re coming from top firms like Female Founders Fund and Lerer Hippeau, diving into growth, consumer, and health. Oh, and they still find time for pickleball. 🏓 Meet the young investors defining the Big Apple’s next chapter in venture: →1. Layla Alexander VC firm: Female Founders Fund She is focused on the care economy, enterprise climate tech, and healthcare, with her portfolio including Co-Star and Cay Skin. →2. Lori Berenberg VC Firm: Bloomberg Beta One of the features she led at MongoDB as a product manager is now awaiting a patent. →3. Alex Chung VC Firm: Chai Ventures She focuses on women’s health, a sector she sees as having untapped potential for innovation. →4. Besart Çopa VC Firm: Antler As a founder-turned-principal investor, his own entrepreneurial experience has shaped his approach to supporting founders. →5. Ethan Daly VC Firm: Shine Capital He was recently promoted to partner at Shine. →6. Marina Girgis VC Firm: Precursor Ventures She’s known for quickly picking pre-seed companies and streamlining the investment process, with a notable pick being AI security startup Edera. →7. Laura Hamilton VC Firm: Notable Capital At Notable, she focuses on data, cloud infrastructure, and cybersecurity, with a particular interest in agent infrastructure. →8. Emily Herrera VC Firm: Slow Ventures She took a forward-thinking approach to creator economy investing before it became widely popular. →9. Bryce Johnson VC Firm: Primary Venture Partners He’s a strong advocate for diversity in venture capital. →10. Will McKelvey VC Firm: Lerer Hippeau He launched a student venture fund at Berkeley, which continues to make investments. →11. Mason Murray VC Firm: New Enterprise Associates (NEA) He’s made six investments, including beehiiv and Twelve Labs. →12. Zehra Naqvi VC Firm: Headline Ventures She runs the popular venture capital newsletter No GPs Allowed, which helps connect investors in New York. →13. David Ongchoco VC Firm: Comma Capital He co-founded Comma Capital, investing at the pre-seed and seed stages. →14. Alexandra Sukin VC Firm: Bessemer Venture Partners She’s a vice president at Bessemer, with investments in fintech Truebill and enterprise companies like Unito and Rewind. →15. Mark Xu VC Firm: Lightspeed He became one of the youngest partners ever at Lightspeed Ventures. →16. Vincent Zhu VC Firm: General Catalyst He’s made a name for himself by hosting events and helping founders make valuable introductions. Thanks to TechCrunch for the info. PS: Check out our weekly newsletter for startups investors at the link in the comments 👇

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Our fireside chat with investor and creator Sahil Bloom is almost at capacity. Thanks to your demand and feedback, we're going to open it up to everyone. Previously, we had reserved spots for founders and future founders, but it turns out a lot of people in NYC read Sahil's Curiosity Chronicle newsletter. If you want to come, RSVP link is in the comments. We'll discuss how Sahil reached >800,000 subscribers for his quickly growing newsletter, The Curiosity Chronicle. Here's what else we'll talk about: - How to transform your voice into a business asset - How to build systems to build an online audience - How to execute your strategy over long periods of time - The Pillar Method: How, when, and what to post - How to write a compelling hook - What kind of content to create - Best newsletter strategies - The future of the creator economy

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Hi everyone! I don’t share too often on here, but we’re at a very exciting moment at AptDeco, and I wanted to let you all in on it. AptDeco opened a community investment round and the response has been incredible. We’ve raised over $2M so far from institutional investors, customers and supporters. Nothing is more validating than customers doubling down with their own capital. And now, I’m inviting you, my network, to be part of our journey. When we started AptDeco, we set out to make buying and selling furniture easier. Over the years, many of our competitors have come and gone, but AptDeco continues to thrive. Why? Our technology, logistics and branding continues to set us apart and that's why major retailers including West Elm, Pottery Barn, La-Z-Boy, Article and 30+ more have partnered with us. The beauty with this investment round is that anyone can be an investor. Learn more and invest directly at wefunder.com/AptDeco.

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Excited to be part of NY Tech Week! 🎉 Come see me and let's talk tech. Whether you have questions, want to start or scale your business, or are interested in a quick intro to AI as a productivity tool, drop by and say hello! Let's innovate together. 🚀 #NYTechWeek #Innovation #AI #BusinessGrowth

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NY friends! Please come see me at Tech Day on my panel discussing the future of the NY tech ecosystem and what I hope to bring to it!

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For Q2 2024, "Around 77% of large deal value went to companies in the four top VC hubs: SF, NYC, LA, and Boston." - Axios Would be curious to know if this is in line with the historic average or if it's trending up/down. Does a startup increase its chances of funding/success if it's located in one of these hubs? It seems like it's a question of whether you want to be a big fish in a small pond or a small fish in a big pond. Peter Walker may have some insight here :) #vc #startups

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At the #SEENSummit2024 in NYC, I had the privilege of joining The New VC Playbook panel with Gabby Cazeau (Harlem Capital), Morgan Blumberg (M13), and Desiree Almodovar (AlleyCorp). One of the biggest takeaways from our conversation was how tough it really is out there for entrepreneurs right now. With interest rates persisting, tighter funding, and investors playing it safe, it’s a grind to even get a foot in the door—especially if you don’t have the right connections. The reality is, the bar is higher, and the road to securing capital is getting longer and harder. We talked about how to keep pushing through, strategies to get funding, and why it’s critical to support founders who’ve been overlooked for too long. It’s tough, but the drive to change the game is what keeps us going. Shoutout to Tech:NYC, Visible Hands, and everyone who showed up and made this summit an honest, energizing conversation about what it really takes to make things happen. #Entrepreneurship #Growth #Innovation #Startups #VC

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NYC is absolutely one of the best places in the world for founders and not just for the most obvious reason… Investor, startup, talent, and prospective client density is absurd there but that’s not it… What makes NYC truly special is the willingness of people to help each other without asking for anything in return. Business karma (!) exists and is thriving in NYC! I realize from traveling across the world, that this doesn’t exist in most other places. In fact, if you try to help, people are so suspicious of you that they won’t accept it. As we know from Adam Grant, effective giving is not only an altruistic endeavor, there is some return. But it is not so transactional that it demands an immediate reciprocation, nor even from the same recipient. This is also what I loved about Techstars (kudos to David Brown, David Cohen, Brad Feld, and Jared Polis) and their #GiveFirst mentality. It’s not location or culture dependent too. I’ve seen it as far as Kyiv, Ukraine, and Talinn, Estonia, in communities like LIFT99 / LIFT99 Kyiv Hub (shouts to Ragnar Sass). Adding more cities to my list of places travelled, I have really come to appreciate this mentality more and more. What other cities and communities engender this attitude? Link/write in comments pls.

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Consumer founders in SF come check out our event next week and register below

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WSJ piece by Dalvin Brown is my highlight for this week's "Read the News" which looks at the cross section of tech, economics, politics, and PR/media relations. All four are in this piece with highlights of the tech companies making it easier to lend funds to friends and family along with the question of how regulation and taxes come into play. Way to go Dalvin Brown! #readthenews

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New York, New York - if you can make here you can make it anywhere We have been retained by 2 amazing startups in the NY. To find Account Executives <---- Both have tremendous funding Both looking for hunters that want to be part of something with a career path. 1. Must have a track record of selling into the Banking/ REIT / Asset Management world - You will be selling a SaaS solution that not only protect and dramatically reduces risk for banks but actually improves their profit and revenue. Essentially a must have solution -already used by some of leading banks, and Financial services companies. 2. Disruptive AI - Embedded data/ analytics and next gen AI. Imagine using AI with 100% accurate information - no more drift no more hallucination, just accurate information. This is built by some of the brightest minds in the AI space enabling business users get answers to questions that they may not even thought to ask. - Imagine having a World class business analyst on your desk to answer and create documents for you in seconds. - This is a company taking the space by storm - already used by Tier 1 companies across all industries. Check out these an other listenings at www.CornerstoneSearch.com

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