Matt Lerner

Hosting your first offsite takes most founders a long time to get to. But this one did it in under 2 years. Patrick Cleary, President and Co-Founder of Paul Street and a key member of the founding team at Wayflyer, shared the BTS of building not 1, but 2 transformative businesses on our latest episode. From driving partnerships and growth strategies at Wayflyer to scaling Paul Street into a leading affiliate-focused marketing agency, Patrick's not scared to redefine how brands grow and scale. In this episode of Turning Pro Podcast, Patrick unpacks how it all went down hosting his first team offsite with over 20 employees, how to balance profitability with growth, the power of compounding networks, and more. Don't miss out on hearing from the Director of Partnerships of a billion-dollar company. We breakdown... → How a simple conversation turned into a multi-billion-dollar company. → How Wayflyer became the fastest-growing Irish startup ever. → Why Patrick left Wayflyer to launch Paul Street. → How networking built Patrick's career and 2 companies. → The one thing most agencies get wrong when trying to scale. → How to delegate and build a high-trust team that operates without you. → Why Paul Street is obsessed with retention. → How a company offsite made Patrick realize he had built something special. And much, much more. Check out the full episode here: https://lnkd.in/gS_3rdki

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VC's can be incredibly "invaluable" at times... The influence of VC funding is a massive contributing factor to the flawed GTM approaches of many SaaS companies. I see this daily with misaligned incentives and short-term focus. They still prioritise growth-at-all-costs over sustainable business, often pushing their investments to scale quickly to justify high valuations and secure the next funding round, which can lead to inefficient or poorly thought-out GTM strategies. Or overfunding them which masks weakness and props up fundamentally flawed businesses. All this does, is delay the need to refine GTM processes. And the worst one of all, they pressure them to follow outdated B2B playbooks. Heavy reliance on outbound sales, MQL (marketing qualified lead) funnels, and siloed marketing/sales teams. I spoke to one company yesterday who has 46 SDRs.. 46! VCs, drawing from past successes to push founders to adopt these legacy tactics even when they’re misaligned with modern buyer behavior or market conditions is a problem It leads to stifling innovation in GTM, forcing companies into inefficient models that don’t reflect how customers actually buy today. Time for change #meetmagic #saas #GTM

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Most founders that we engage with at Settle talk about raising the bar. Matt Mullenax from Huron flips that thinking: it’s all about raising the floor. In this week’s Founder Friday, Matt shares why leveling up every part of your business, from talent to creative, is the real unlock for growth. From his early days at Bonobos with Andy Dunn to seeing Huron on shelves at H-E-B, his journey is a reminder that persistence, strong fundamentals, and great mentors matter just as much as ambition. 1. What’s one thing you wish you knew a year or two ago? MM: The importance of constantly 'raising the floor' across your business. Whether that's hiring better talent, leveraging better creative, crafting better offers, or improving on brand comms. Raise the floor across the board and settle for nothing less. Sounds easy on paper and in principle, but difficult to action on. But once you do, your business will grow. 2. What was your strategic hack to customer growth? MM: We've taken a bit of a different approach this year in terms of cleaning up or solidifying our business *outside* of pure growth initiatives. Why? Now we have more margin, flexibility, and creativity to leverage in our growth sandbox. So, in a circuitous manner, we've 'hacked' growth by continuing to move the needle on other aspects of the business to create bigger and better opportunities (and a longer leash) for growth. 3. What has been the most rewarding moment in your journey as a founder? MM: Really difficult to pinpoint *the* most rewarding moment. Seeing our products on physical shelf recently at H-E-B was a huge moment. And any time we see Huron in the wild — my friend texted me a photo of a guy with a Huron Tote Bag walking in New York, for instance — those are always very cool moments. 4. Who has been your biggest mentor or role model in your entrepreneurial journey? MM: I've been so fortunate to work with and learn from some of the best founders inside and outside of the ecommerce space. Andy Dunn is the first to come to mind. I had the pleasure of being an early employee at Bonobos starting in late 2008. Andy really ignited my passion for early-stage consumer. Andy is one of our investors. He's oftentimes the first to respond to investor updates with positive words but won't hold back from challenging, too (a great balance). As a friend, Andy has helped me grow and mature personally and professionally over the past 15+ years. 5. Any advice you can share to up and coming brand founders reading this?  MM:  Today's struggles are tomorrow's strengths. Starting a company is daunting and challenging. But there are so many learnings and positive experiences to be had. Believe in the mission and believe in what you're building, to an irrational and uncompromising level. Drop a comment or question to share with Matt below!

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Evolving Web turns 18 today 🥳 And as one of the co-founders, that means I've technically had the same job for 18 years... But in no real sense is my job the same as it was in 2007 when Alex Dergachev and I started the company. We literally started it out of our student apartment when we were graduating from McGill University. We were swept up in enthusiasm about tech startups and open source, which became a big part of our identity and culture. Some things I’ve learned as a woman in tech, an open source contributor, and a founder: 1️⃣ Talk about what’s hard. Whether it’s growing pains or project failures, talking about your challenges and what doesn't work is part of the learning process. 2️⃣ Stay curious. The technology and tools look completely different from 18 years ago. A willingness to keep learning and being open to change is essential. 3️⃣ There an abundance of digital work. The need for thoughtful digital strategy is huge. We don’t need to hoard knowledge. 4️⃣ Impact happens at every level. We’ve worked with institutions that are changing lives—through healthcare, education, and public service. But the impact is also personal. Clients who get energized by our training sessions. People who’ve built entire careers with Evolving Web. Teammates who light up when they learn something new. 5️⃣ Open source = striving to do it right. When you're building in an open source environment, what you create is designed to be used by a big community. This means, you pay more attention to the details, and helps you scale up. Whether creating a slide-deck template, picking a CSS class or machine name, or building a design system, there's value in doing it right. 6️⃣ Some of the best lessons come from teaching. Our training program has brought me into dozens of higher ed, government, and enterprise organizations and other agencies across North America, and I've learnt so much about different work cultures from this experience. 7️⃣ Partnerships matter. We’ve built long-term relationships with organizations we admire. We’ve learned from fellow agencies. And we’ve had the joy of contributing to the Drupal and WordPress communities alongside some brilliant people. 8️⃣ Never stop learning. Mentorship, open source contribution, community events, investing in people—all of it keeps me growing. Shoutout to our EvolveDigital + EvolveDrupal Summits that give me a chance to teach and learn. #EvolvingWeb #Drupal #OpenSource #DigitalStrategy #EvolveDigital

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"If you had a Jerry Maguire moment and said 'f*ck it all, I'm starting from scratch'..." I think my question broke Alexander Matthey's brain for a second (sorry!) His answer reveals some FACTS about building companies that he applied at Parloa but also Adyen and Glossybox before: "All of these things are very difficult to be built in afterwards." What "things" is he talking about? - company culture - hiring standards - product architecture - GTM focus - execution discipline You can't retrofit excellence, and you can't add speed to a slow company. You can't build quality on top of technical debt. the decisions you make in month 1 echo for years. once you've built it wrong, "fixing it later" becomes your full-time job. What are you building into your foundation that will be impossible to change later? listen to the full episode out now https://lnkd.in/gDspbaTF

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There's a new breed of founders emerging, and they're filling gaps faster than the market can create them. The market has always had gaps. You know them. The frustrations that make you think "why doesn't this exist?" The workflows that could be smoother. The tools that should have been built years ago. The datasets that should be readily available. For decades, these gaps just... sat there. Unfilled. Obvious. Waiting. Not because no one saw them. Everyone saw them. But because filling them required teams, capital, years. The math didn't work. So the gaps stayed. Until now. --- I call them fast-cycle founders. Some call them "vibe founders." They're not trying to build unicorns or billion-dollar exits. They're doing something simpler: Spot a gap. Build in weeks. Ship it. Fill it. Move on to the Next. Why is this suddenly possible? Because with AI tools, what used to take 5 engineers and 6 months now takes 1 person and 3 weeks. The creation cycle hasn't just shortened. It's collapsed. --- Look at 2024-2025. Indie hackers building weekend projects hitting $50K MRR within months. Solo founders launching SaaS tools that would've needed entire teams two years ago. Browse platforms like acquire.com. Scroll through X threads and Reddit discussions. The pattern is everywhere. Those gaps that sat there for decades? They're getting filled. Fast. --- Here's the shift: **Building is becoming a commodity.** When AI makes building as easy as Canva, coding isn't the differentiator. What matters? Spotting what needs to exist. Reaching the people who need it. When anyone can build in weeks, the hard part isn't the product. It's getting people to care. **Attention is the new moat. Distribution is the new defensibility.** --- This changes how we should think about startups. Stop thinking like you're building monuments. Start thinking like creators. Rajamouli spends 2-3 years making RRR. Then moves to the next project. He doesn't expect one movie to generate revenue for decades. Why should your startup be different? --- Product shelf life is shrinking. But when creation is this cheap and fast, you don't need a 10-year shelf life. Stop optimizing for "How do I make this last forever?" Start optimizing for "How do I capture value now and build the next thing?" Portfolio over monument. Rhythm over permanence. --- This age belongs to the fast-cycle founders. The ones who can spot a gap that's been sitting in the market for years. Build a solution in weeks, not years. Distribute it to the people who've been waiting for it. And move to the next gap when this one's filled. --- The market has endless gaps. AI has made filling them faster than ever. The question is: Which gap will you fill first? #AI #Vibe #Startup

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Dogooders and accelerators staffed by professional delivery people who have never founded or operated startups are dangerous. I've just come off the phone from a founder who was advised to raise £xm by the mentors on an accelerator. These are people who sell themselves as knowledgeable in this space but are anything but. Th problem is the only needed 25% of the amount they advised (including buffer). If he raises this amount at this stage, he'll likely have to give away a third of his business. Which is far far too much far far too early. A little knowledge is a very dangerous thing indeed.

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Most founders fail at fundraising because they misunderstand the game. They obsess over decks. They memorise investor scripts. But here’s the reality: If you need to convince someone to invest, you're already behind. I’ve raised, invested, and sat on both sides of the table for 20+ years. The founders who raise fast, raise well—and raise again—aren’t better pitchers. They’re better builders. They build companies that investors want to say “yes” to before the meeting starts. Here’s what separates them: 1. They’re Fluent in Investor Language ↳ They align the company’s future to the investor’s mandate—without selling out the mission ↳ They translate traction into ROI, not emotion 2. They Use Capital to Add Multipliers, Not Crutches ↳ Fundraising is used to scale validated momentum—not to fix leaky systems ↳ They raise after building engine efficiency, not instead of it 3. They Hire as a Force Multiplier, Not a Badge of Progress ↳ No bloated headcount to “look” like growth—only hires that accelerate systems ↳ They scale workflows first, then plug in people to amplify—not patch gaps 4. They Own Their Numbers Like Founders, Not Just Presenters ↳ Metrics aren’t just slide bullets—they’re embedded into every weekly decision ↳ They can navigate CAC, LTV, burn, and runway without the crutch of a spreadsheet 5. They Don’t Chase Funding—They Create Optionality ↳ Their business model, pace, and decisions signal: “We’re raising because we can, not because we must” ↳ Desperation kills valuation. Leverage builds it. The reality is: You don’t need a perfect pitch to raise capital. You need a business that already feels investable. Most founders never learn this. The ones who do? They build wealth, not just startups. — DM me if you’re prepping for a raise and want a second set of eyes on your investor readiness. Follow me Ben Botes for weekly insight drops on scale, capital, and leadership. Let’s build companies investors chase—not the other way around. #Fundraising #Startups #VentureCapital

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450 million email links have been tracked through Bunce in the past 7 months. That's along with 1.1 billion user message actions (opens, clicks etc) from 55 million messages sent 🤯 Bunce builds customer engagement tools for modern software companies, and Baobab Network have been proud investors since August 2023. Paul Ayuk, Justus Oseuno and the team now serve blue-chip clients including Burger King, FiberOne Broadband, and Midddleman, who they recently helped achieve a 200% growth in customer engagement. The Midddleman story was so good that they actually published a full case study about it, which you can read more about here: https://lnkd.in/eZS4Kb7p Bunce's platform allows fast growing companies to optimise targeted messaging and automation across emails, SMS and WhatsApp, and also send better in-app notifications that lead to improved retention and revenue growth. If you're building something interesting and want to fine-tune your customer insights, reach out to Paul Ayuk and the Bunce team today 🙏 This is definitely one of the companies we are most excited about right now.

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Leaving the Big4 for startup life was one of the best decisions I've made 😄 But leaving all that structure and bureaucracy behind had a drawback... - How do you get the training, support, progression you need? - What should a startup finance team actually do? - What's the role of a CFO in such a small business? - How do you get to the top job? We know these are questions people have when they're looking to join or build a startup finance team. So, we've asked our good friends Corinne and Ankush to join Dan for a webinar chat next week to understand their journeys and what you should look for from your startup CFO. For founders and finance folk in startups. Sign up here: https://lnkd.in/gYvHgWti

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We’ve been sharing glimpses of how AI is changing the way Carta works - both internally and for our customers. Here’s another one I’m really excited about. Historically, if our fund admin team or a GP wanted to get a clear picture across all their funds, it required jumping between individual fund views. Even something simple like checking a bank transaction  could take way too many clicks. Over the past few weeks, we’ve been testing an internal AI tool that can surface answers across an entire firm. Want to know if a wire went out to a specific beneficiary? Need to see the related journal entries? Just ask. Right now, this is a tool for our team. But we’re building toward a future where GPs can get answers like these instantly - without digging, waiting, or switching context.

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