Matt Robinson

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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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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No matter if DeepSeek spent 5 million, 100 or 1billion - LLMs become better while becoming cheaper. Cheaper to build and cheaper to run. DeepSeek is another massive step towards the commodisation of LLMs. As margins squeeze for the LLMs, they will seek margin within AI applications, hence they build their own agents, computer use etc. It is what they differentiate themselves from other LLMs. So to build a business that has a moat, you have to find an industry specific AI application with a non-public dataset, maybe even an offline data set. Something not even DeepSeek has access to. And then you can do magical things, AI applications for the real world. That help offline businesses (=90% of businesses) do better. The great thing is: you can build this from anywhere. Even outside the US and China. Even in the EU. (and yes we still have to undo the AI Act urgently so that we can create global AI application winners, just regulate high risk AI but leave the rest unregulated. Ursula von der Leyen & Henna Virkkunen & Thierry Breton & Margrethe Vestager, European Commission ) https://lnkd.in/drwA-Jnp

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Whilst Augnet wasn’t the unicorn exit we all hoped for, I learned a lot about fundraising, including lessons from my own mistakes, that I still see many founders struggling with today. When we launched in 2019, our first raise was a success, raising £1.3m at a £7.5m pre-money valuation. The biggest factor was momentum. * We solved a real-world problem. * We were recruiting impressive, highly credible, talent. * We had strong engagement with big-name customers. A raise has to ride on the back of momentum. If revenue is flat or customer acquisition isn’t continually proving product–market fit, investor sentiment will stall. Fundraising isn’t just about a pitch deck or a great product. You can’t appear to be in “hibernation” waiting for funds. You need to show that things are already moving fast enough that cash will accelerate the journey, not start it. And yes, the investor universe looked very different in 2019 compared to today. Which only makes me believe this more.

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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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The real threat to your business isn’t AI. It’s the new founder using AI to build faster than you can react. These are AI-native startups, shipping daily, scaling without headcount, and skipping the bloated legacy systems that slow incumbents down. Once they nail distribution and the tools get just good enough to outperform you on execution, it’s done. You don’t catch them. You buy them. This is already happening. In South Africa. There’s never been a better time to build a startup, and never a more important time for incumbents to track what’s being built. That’s what we do...every day. Subscribe to The Open Letter and stay sharp on SA’s startup, tech and business moves.

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Our data shows a clear pattern: Founders outside of financial hubs give away more of their company, right from the start. A founder in Wales raising £500k might be diluted 22%+ But a founder in London raising the same amount would be closer to 13% And that single round can set your company on a certain trajectory: Less equity for the founder, less upside for early employees, and even less room for future investors. The downstream effects are massive and long-lasting. It isn’t to do with the quality of talent or ideas. It comes down to the limited number of fundraising options available in those areas. Being further from financial hubs means there are fewer angels, VCs, and corporates at your disposal. And it’s why regional founders often face tougher fundraising journeys, even when they’re building equally strong businesses. In 2025, geography shouldn’t be a factor when it comes to dilution (especially in a country as small as the UK) but the numbers tell a different story. My advice for founders outside of financial hubs is this: Don’t spray-and-pray. Do your research, identify and target the most relevant investors in your space (regardless of their location, especially if you can demonstrate traction in the geographies where their fund is based), and avoid over-reliance on a handful of local players. Otherwise, you risk giving away too much, too soon. At shipshape.vc, we’re committed to levelling that playing field - helping founders anywhere, not just in London or New York, raise smarter and protect more of the companies they’re working so hard to build. #Fundraising #Startups #VentureCapital #Entrepreneurship #RegionalFounders #Equity #ShipshapeVC

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How should founders pick the right investors? Last week I met one of the most exciting founders I’ve seen in a while. Brilliant product, brilliant team, and as soon as I heard the vision and saw what they had built, I knew this was a business with huge potential. No surprise, they’ve now got a lot of investor interest. A nice position to be in. But also a dangerous one if you choose the wrong partners. 👉 So how should founders pick investors who will help them grow, not hold them back? Here are a few practical questions I always encourage founders to ask: ✅ Will this investor open doors to the right business development opportunities? ✅ Do they bring real go-to-market experience, or just capital? ✅ Can they help you think through which geographies to expand into (vs chasing easy but low-value markets)? ✅ Are they equipped to advise on strategic partnerships - think AWS, trade associations, key channel partners? ✅ Will they push you to build an operationally ready, scalable platform, or just chase quick metrics? ✅ Do they understand the nuances of selling into complex sectors, e.g. financial services, critical infrastructure, healthcare, where regulatory and security demands are key? ✅ Will they help you prepare for a strong Series A / Series B, not just this round? Sometimes the investor who offers the biggest cheque is not the one who will help you win. Sometimes it’s the investor who quietly understands where your business is today, and what you’ll need 12, 24, 36 months from now. 👉 If you’re a founder and you’re in this position, lots of interest, but unsure who will really help you scale, expand, and build real enterprise value, let’s chat. Sometimes it’s not about what you know, it’s about what you don’t yet know you’ll need. Dr. Jacqui Taylor - would love to hear your take: what should founders look for when picking investors? #Founders #TechFounders #StartupGrowth #VentureCapital #ScaleUp #Fundraising

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10 fundraising errors that kill deals before they start I had the pleasure of collaborating with Marc Penkala (altitude) and Alexander Estner (MRR Unlocked) on a Blueprint for Securing Early-Stage Funding in 2025. 🚀 We’ll be sharing the full guide later this week and tried to break down everything about startup fundraising, e.g. the most common mistakes we have been seeing over the last years: ❌ Mistake #1: Pitching too early Lack of proof points = Lack of credibility ✅ Wait until you have real proof points ❌ Mistake #2: Too many iterations Pivoting during fundraising screams "we don't know what we're doing" ✅ Lock in your narrative before going to market ❌ Mistake #3: Founding team changes during the process Team changes = instant red flag ✅ Resolve team issues before raising ❌ Mistake #4: Overpromising projections If you don't follow through, it kills your credibility. ✅ Be realistic with forecasts ❌ Mistake #5: Running a messy process Dragging it out for 12+ months means lost momentum ✅ Set clear timelines and stick to them ❌ Mistake #6: Raising without a plan Fundraising just for runway isn't enough. ✅ Have crystal-clear use of funds ❌ Mistake #7: Not understanding investor expectations ✅ Research fund size, check sizes, and returner expectations ❌ Mistake #8: Spray and pray outreach Generic emails show a lack of preparation ✅ Personalize every single outreach ❌ Mistake #9: Starting too late Less time forces you to take desperate decisions ✅ Start 6-9 months before you need capital ❌ Mistake #10: Fluff-heavy pitch decks Jargon doesn't impress investors ✅ Focus on the crucial information only The founders who avoid these mistakes raise faster, on better terms and from the right investors. Which ones are you guilty of making? We turned our years of angel and VC experience into an actionable mrrunlocked guide on how to get your first funding round in 2025 and hope it’s helpful for you. Watch out and thanks to Alex for the great initiative and major work.

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