At just 27 years old, Harry Stebbings commands attention in venture capital circles that most seasoned investors spend decades trying to cultivate. Speaking at SXSW, the founder of 20VC and one of Europe’s most influential tech voices shared the unconventional strategies that transformed him from a “temporarily embarrassed 17-year-old” with no money or connections into a media mogul whose podcast has become essential listening in Silicon Valley.
Stebbings’ journey offers a masterclass in leveraging content creation as a business development tool, while his perspectives on European entrepreneurship highlight critical gaps that could determine whether the continent can compete with US and Chinese tech dominance in the coming decade.
The Cold Email Formula That Opens Doors
Perhaps no aspect of Stebbings’ early strategy was more crucial than his approach to cold outreach. “Everyone sucks at cold email,” he observed, describing the verbose, self-aggrandising messages that typically land in spam folders.
His formula was radically different: “Hi, Josh. I saw you made this investment. I scaled my business in a similar category to 6 million in revenue. I would love 10 minutes of your time.” Three lines. No fluff. Clear value proposition.
The persistence behind this approach was extraordinary. Stebbings famously sent 53 emails to Marc Benioff, CEO of Salesforce, varying each message with different personal touches – “different whiskey that we love, different favourite holiday spot, different lists” – until the 53rd attempt finally broke through.
This systematic approach to relationship building extended to his podcast growth strategy. “I used to do cold DMs to every Twitter follower up until 50,000 followers. Every night from 1 and 2 AM,” he revealed, personally crafting messages that acknowledged specific details about each person’s background.
For entrepreneurs struggling with business development, Stebbings’ approach demonstrates that success often comes down to volume, persistence, and genuine research rather than clever tactics or insider connections.
Media as Customer Acquisition Engine
While most entrepreneurs view content creation as a marketing expense, Stebbings repositioned it as a customer acquisition strategy. The insight was profound: rather than asking busy executives to “pick their brains” – which sounds transactional – he offered them a platform to share their expertise.
“If you say, ‘Hey, I’d love to interview you for my podcast,’ people were much more willing to do it,” he explained. This approach solved a fundamental business development challenge: how to get meetings with people who don’t need your money or services.
The framework extends beyond podcasting. Stebbings advocates that any business builder should consider media as their primary relationship-building tool. For a legal AI company, he suggested, “I would choose media as a customer acquisition engine” by interviewing the biggest law firm partners globally, building relationships through content, then naturally introducing their software solution.
This strategy trades attention for expertise, allowing entrepreneurs to access insights from industry leaders who might otherwise be unreachable. It’s particularly powerful for young founders who lack traditional credentials but can offer valuable exposure through their platforms.
The Comfort Versus Confrontation Divide
One of Stebbings’ most significant insights concerned interview methodology, which has broader implications for business relationship building. He contrasted his approach with traditional journalism, where reporters are “trained to make people feel uncomfortable on stage… to ask them hard questions to grill them, to kind of put them in a corner.”
His philosophy was entirely opposite: “My job is to make someone feel incredibly comfortable in my company, so they’ll share everything.” This approach requires developing what he calls “the single greatest skill” – the ability to listen deeply and care about how others feel in conversations.
For entrepreneurs, this represents a fundamental choice in relationship building. The confrontational approach might generate short-term insights or headlines, but the comfort-first methodology builds long-term trust and access. In venture capital, where relationships determine deal flow and portfolio support, this distinction becomes business-critical.
Europe’s Innovation Imperative
Stebbings’ most passionate commentary concerned Europe’s competitive position in global technology. Despite running a successful business from London, he acknowledged wondering “what would life be like if I was in America?” – a reflection shared by many European entrepreneurs who feel constrained by their ecosystem’s limitations.
However, rather than advocating exodus, Stebbings argued for intentional ecosystem building. “We need to tell people that they can build great businesses here. And we need to not stop people from building here,” he emphasised, pointing to cultural tendencies to discourage ambitious projects.
His diagnosis of European venture capital was particularly striking: “There is so much money in European venture, so much. The prices are ridiculous, millions going into companies that should not get them.” The issue isn’t capital availability but talent retention and cultural support for risk-taking.
The solution requires multiple interventions: policy changes to support entrepreneurs, cultural shifts toward celebrating ambitious failures, and what he termed reducing transactional thinking. “People always ask, ‘What are you getting for this?’ I just think you’re great, so I just want to help. And that’s it. There’s not a quid pro quo.”
For European policymakers and ecosystem builders, Stebbings’ perspective suggests that regulatory improvements alone won’t solve the competitiveness gap. Cultural transformation – toward supporting bold visions rather than discouraging them – may be equally important.
The Content Evolution Challenge
Stebbings also provided crucial insights into how content consumption has evolved, with significant implications for entrepreneurs using media strategies. “Five years ago, you would do a show with someone on management lessons… I promise you people don’t give a shit about management lessons anymore,” he observed.
Modern audiences want two things: “They want to be told a story. They want to be inspired.” This shift from educational to inspirational content reflects broader changes in how people consume information in an attention-constrained environment.
For entrepreneurs building content strategies, this evolution demands rethinking value propositions. Rather than focusing on tactical advice or industry insights, successful content increasingly needs emotional resonance and narrative structure. The implication extends beyond media: all business communications – from pitch decks to product marketing – must account for audiences seeking inspiration over information.
Risk-Taking Across Life Stages
Perhaps Stebbings’ most nuanced insight concerned risk tolerance across different life circumstances. While celebrating his own early success, he was careful to acknowledge the relative ease of his position: “I was 17 in a bedroom. If it didn’t work, I was going to law school. It’s not that bad.”
His deeper respect was reserved for entrepreneurs with families and mortgages who “go, ‘I’m going to leave my job’ to start a business that is 98% destined to fail. You are unbelievable… that’s an entrepreneur.”
This perspective offers important guidance for aspiring entrepreneurs across different life stages. For young professionals, Stebbings’ story demonstrates how early career risks can compound into significant advantages. For more established professionals, his recognition of their courage suggests that different strategies – perhaps more conservative approaches or longer transition periods – might be appropriate without diminishing entrepreneurial ambition.
The Vision Development Framework
Stebbings also addressed one of entrepreneurship’s most persistent challenges: developing authentic vision when starting from uncertainty. His approach involved progressive expansion rather than grand initial declarations.
“My vision was to get a job better. That’s what my vision was,” he admitted about his early podcasting days. Success enabled larger ambitions: from getting any job to working at a prestigious firm, eventually to building a media empire and supporting European entrepreneurship.
The methodology involves what he called being “your own little toddler, being like, ‘But why? Why is this guy blue?’ ‘Okay. Well, why does life work that way?’ Just keep asking until you get to that root.”
For entrepreneurs paralysed by uncertainty about their ultimate purpose, this framework suggests starting with immediate, achievable goals while maintaining curiosity about deeper motivations. Vision can emerge through action rather than preceding it.
Looking Forward: Implications for Global Tech Competition
Stebbings’ insights arrive at a crucial moment for global technology competition. As US-China tensions create opportunities for third-pole innovation hubs, Europe’s ability to retain and develop talent becomes strategically important. His success demonstrates that European entrepreneurs can build globally influential platforms, but his concerns about ecosystem limitations highlight persistent challenges.
The broader lesson extends beyond geography. In an increasingly competitive global market, success increasingly depends on relationship-building capabilities, cultural adaptability, and the ability to leverage new media channels for business development. Traditional credentials and insider networks, while still valuable, are becoming less decisive compared to content creation skills and authentic relationship building.
For the next generation of entrepreneurs, Stebbings’ playbook offers a compelling alternative to conventional business development approaches. Rather than waiting for perfect timing or optimal credentials, his story suggests that systematic outreach, authentic relationship building, and content-first strategies can create opportunities that traditional approaches might miss.
As technological advancement accelerates and competition intensifies, these relationship-building capabilities may become the defining advantage for entrepreneurs seeking to build lasting, influential businesses in an increasingly connected global economy.
