- Raise like a Pro
- Posts
- Raise like a PRO - To raise or not to raise
Raise like a PRO - To raise or not to raise
...that is the Founder's Dilemma.
David Levine
May 01, 2025
Welcome back to Raise Like a Pro dear reader! ; a newsletter to help you do exactly that.
I'm David, and unlike most people giving fundraising advice, I don't just talk about raising money – I’ve been there as a founder and now I spend my day raising money for startups all over the world from investors all over the world.
I've closed millions in new investment in the past few months alone for startups - and I’m going to teach you how to do it without needing someone like me. This is my playbook; the operational, tactical and yes - sometimes boring stuff you need to do each and every day to raise your round.
No nonsense, no fluff and definitely no fuzzy sheep.
Table of Contents
My promise to you
Every piece of advice in this newsletter comes from actual experience: deals I've closed, terms I've negotiated, and strategies I've refined through real-world application.
I'm not here to give you startup platitudes or generic advice. Instead, you'll get practical, actionable tactics that you can implement immediately in your fundraising journey.
The goal? To help you raise money faster, at better valuations, while protecting your interests and your time.
– David
Overview of main topic
By now you know - I raise money for a money. For founders all over the world from investors all over the world.
And I get paid for it - because the mortgage doesn’t pay for itself!
Hence the look of surprise, shock and horror when I suggest to a founder that they should not actually raise - or raise less than they think.
But it’s true - raising is merely a milestone on the way to success for those businesses that need to raise capital.
But not every business should. Even if that means I get paid less.
We’re going to unpick that below!
💰 Deals that caught our eye this week
🧬 Deepull (Barcelona, Spain)
Sector: Medical diagnostics
Round: €50M Series C
Summary: Developing non-culture diagnostic tools for rapid pathogen detection in whole blood.
Investors: Columbus Venture Partners, Panakès Partners, Mérieux Equity Partners
🔗 Read announcement
👓 IXI (Helsinki, Finland)
Sector: Smart eyewear
Round: $36.5M Series A
Summary: Building prescription glasses that automatically adjust using eye-tracking and liquid crystal lenses.
Investors: Led by Plural, joined by Tesi, byFounders, Heartcore, Eurazeo, FOV Ventures, Tiny VC
🔗 Read announcement
⚡ iwell (Utrecht, Netherlands)
Sector: Energy tech
Round: €27M
Summary: Provides modular battery storage and energy management for commercial/industrial use.
Investors: Meridiam (lead), Invest-NL, Rabobank
🔗 Read announcement
🔄 DePoly (Sion, Switzerland)
Sector: Plastics recycling
Round: $23M Seed
Summary: Breaks down PET and polyester plastics for recycling using proprietary chemical tech.
Investors: BASF Venture Capital, Beiersdorf Venture Capital, Zürcher Kantonalbank
🔗 Read announcement
👕 eeden (Münster, Germany)
Sector: Textile recycling
Round: €18M Series A
Summary: Chemical recycling for the fashion industry.
Investors: Forbion (lead), Henkel Ventures, NRW.Venture, TVF, HTGF, D11Z Ventures
🔗 Read announcement
🏦 Sprive (London, UK)
Sector: Fintech / Mortgages
Round: £5.5M
Summary: Helps users make faster mortgage repayments to save money.
Investors: Ascension (lead), Velocity Capital, Two Magnolias, Channel 4 Ventures
🔗 Read announcement
To raise or not to raise: The Founder's Dilemma
Should you even raise?
On one level I’m the last person you should be asking. I help startups raise - that’s how I get paid. So you’d expect me to say “of course you should”.
But it doesn’t work like that. Some businesses shouldn’t raise, don’t need to raise or at least - shouldn’t yet.
It's a question that seems to have an obvious answer if you're scrolling through TechCrunch or LinkedIn, where funding announcements are celebrated like Olympic medals. But behind the champagne-popping photos and press releases lies a more complex reality that deserves serious consideration. As someone who does this every day and whose not shy to be direct - I’ll be direct ;)
The Pressure Cooker of Fundraising
There’s insane pressure to raise venture capital these days. Open any tech publication and you're bombarded with headlines trumpeting multi-million pound raises, often accompanied by glowing profiles of founders who seem to have it all sorted. "XYZ Secures £20M Series A Led by Top-Tier VCs." "Former Google Employee Raises £5M for New Startup." These success stories create a narrative that raising venture capital is not just desirable but essential.
The pressure doesn't just come from media. It's also peer-driven. When your fellow founders in the co-working space or WhatsApp group start discussing their funding rounds, term sheets and investor meetings, it's hard not to feel left behind. The question shifts insidiously from "Should I raise?" to "Why haven't I raised yet?" This FOMO-driven approach to company building can lead founders to pursue funding before they're ready or when it's not actually aligned with their business model.
And if you’re not the one raising? It can feel tough.
But perhaps the most potent source of pressure comes from within. There's a certain validation that comes with convincing sophisticated investors to bet millions on your vision. It feels like official recognition that your idea isn't bonkers, that you're not wasting your time, that you're a "real" entrepreneur. This psychological component shouldn't be underestimated - many founders pursue venture funding partly as a form of external validation.
The Milestone Mindset: VC as Achievement
Raising venture capital is undeniably a significant milestoned. It can transform your business, providing the rocket fuel needed to scale quickly, hire top talent, and capture market share before competitors. When deployed correctly, venture funding can accelerate your trajectory in ways that organic growth simply cannot match.
The capital infusion allows you to dream bigger and execute faster. Instead of painstakingly growing your team one affordable hire at a time, you can bring on experienced executives. Rather than limiting your marketing to low-cost channels, you can launch comprehensive campaigns. Product development timelines shrink, and international expansion becomes feasible sooner.
Beyond the obvious financial benefits, venture backing often comes with valuable intangibles. Most VC firms offer access to their networks - introducting you to potential clients, partners, and future investors. Many provide operational expertise, helping with everything from recruitment to strategic planning. These resources can be just as valuable as the money itself, particularly for first-time founders navigating unfamiliar territory.
Not All Roses: The Reality Check
Despite these advantages, raising venture capital is not the unalloyed good it's often portrayed to be. The reality is far more nuanced, with significant trade-offs that aren't immediately obvious when you're caught up in the excitement of a funding round.
Most fundamentally, taking venture money means accepting a fundamental change in your company's purpose. You're no longer building a business that needs to be merely successful - you're building one that must be enormously successful within a compressed timeframe. VCs don't invest for solid 15% annual returns; they need moonshots that return their entire fund. This creates a structural pressure to swing for the fences, even when a more measured approach might be healthier for the business.
This pressure manifests in various ways. You'll likely be pushed to prioritise growth over profitability, sometimes to an unsustainable degree. You might be encouraged to enter markets before you're truly ready or to expand your team faster than your culture and processes can accommodate. The focus shifts from building something sustainable to creating the metrics that will enable the next fundraise.
You've Got a Boss Now (Actually, Several)
One of the most jarring changes for founders post-fundraising is the sudden accountability to new stakeholders. The dream of entrepreneurial independence - of being your own boss - fades as you realise you've essentially taken on multiple demanding supervisors in the form of your investors.
Once you accept venture funding, you're no longer working solely for yourself and your vision. You now have a fiduciary duty to your shareholders, who expect you to maximise their returns. This means regular board meetings where you explain your decisions, defend your strategy, and sometimes receive pushback on your plans. For founders accustomed to autonomy, this loss of control can be difficult to swallow.
Your board will have opinions on everything from hiring decisions to product strategy. While good investors bring valuable perspectives, they also constrain your freedom. Major decisions require their buy-in, and disagreements can lead to tense situations. Gone are the days when you could pivot the business on a whim or take a contrarian approach without explaining yourself.
What's more, different investors may have different priorities. Your seed investor might be focused on product-market fit, while your Series A lead is obsessed with growth metrics, and your Series B backer is concerned about unit economics. Balancing these sometimes conflicting expectations becomes part of your job.
The Accountability Equation
With venture money comes heightened accountability. You'll need to establish formal reporting structures, provide regular updates, and deliver on the promises made during your fundraising pitch. This rigour can be beneficial, forcing discipline and strategic clarity. However, it also creates significant administrative overhead and adds pressure to perform.
The cadence of a venture-backed business is typically measured in 12-18 month increments - the time between funding rounds. Each period becomes a race to achieve the metrics necessary for the next raise. This creates a perpetual cycle of pressure, with founders constantly aware that they're burning runway and need to hit ambitious targets to secure more fuel.
This accountability extends beyond investors to your team. When you announce a large funding round, expectations within the company shift. Employees anticipate accelerated growth, increased resources, and expanded opportunities. If reality doesn't match these expectations, morale can suffer. The funding announcement that seemed like such a triumph can quickly become a burden if the promised growth doesn't materialise.
The Hard Maths of Venture Returns
Perhaps the most sobering aspect of venture funding is how it fundamentally reshapes your exit options. Venture capital operates on a power law distribution - most investments fail, some return capital, and a tiny percentage generate enormous returns that make the entire portfolio profitable. This model necessitates that each successful company in a VC's portfolio delivers outsized returns.
What does this mean for you? It means that even if you build a solid, profitable business worth tens of millions, it might still be considered a disappointment by your investors if they've put in substantial capital at a high valuation. The company that would have made you financially independent as a bootstrap founder might be deemed a failure in the venture context.
This dynamic is exacerbated by liquidation preferences - contractual terms that ensure investors get their money back (or more) before founders and employees see a penny. These preferences, which are standard in venture deals, mean that moderate exits often leave founders with far less than they might expect given their ownership percentage.
The mathematics become even more challenging with each funding round. As you raise more capital at higher valuations, the threshold for a successful exit climbs ever higher. A company that's raised £50 million needs to exit for hundreds of millions just for everyone to be satisfied. Unicorn status (£1 billion+ valuation) becomes not just aspiration but necessity.
The Founder Wellbeing Factor
There's another dimension that rarely makes it into the glossy funding announcements: the immense personal toll of building a venture-backed business. The pressure to perform, the compressed timelines, and the high stakes often lead to significant stress and burnout.
Recent research reveals that 83% of founders believe there are diminishing returns from simply working longer hours, yet many feel trapped in a culture that glorifies relentless hustle. The constant pressure in venture-backed companies can actively harm business performance, with 64% of founders acknowledging this reality.
The venture treadmill rarely slows down. Once you've taken external funding, the expectations only increase with each subsequent round. Founders often find themselves caught in an exhausting cycle of fundraising, execution, growth at all costs, then more fundraising. It's a pace that few can sustain for the five to ten years typically required to reach a successful exit.
Should You Take the Money?
With all these considerations in mind, how should founders approach the venture capital question? There's no universal answer, but here's a framework that might help:
Venture funding makes the most sense when:
Your market opportunity is genuinely enormous
Speed is essential to capturing that opportunity
Your business model requires significant upfront investment before generating revenue
You're building in a winner-takes-most market where scale creates defensibility
You're personally comfortable with the accountability and pressure that comes with VC
Conversely, bootstrapping might be preferable when:
Your target market is substantial but not massive
You can grow organically through revenue
You value control and independence over rapid growth
You prefer building for the long term rather than aiming for a quick exit
You want flexibility to pivot without external approval
The Third Way: Capital-Efficient Ventures
It's worth noting that the choice isn't binary. Many successful companies take a middle path, raising modest amounts of capital while maintaining founder control and reasonable exit expectations. This capital-efficient approach combines some of the acceleration benefits of venture funding with the sustainability focus of bootstrapping.
Some founders opt for alternative financing models like revenue-based financing, which ties repayment to business performance rather than equity dilution. Others take small seed rounds but aim to reach profitability quickly, removing the need for subsequent fundraising unless it's specifically for acceleration.
Conclusion: Eyes Wide Open
Raising venture capital can indeed be transformative for the right business with the right founder at the right time. The resources, expertise, and networks that come with VC backing enable ambitious founders to build category-defining companies that might otherwise never reach their potential.
However, this path demands clear-eyed assessment of the trade-offs involved. The pressure, accountability, dilution, and constrained exit options are real costs that must be weighed against the benefits. Too many founders raise venture capital because it seems like the default path to success, only to realise later that it wasn't aligned with their personal goals or business model.
The most successful founder-investor relationships occur when both parties have aligned expectations and complementary strengths. If you do choose the venture path, focus on finding investors who truly understand your vision and can add value beyond their capital. Remember that not all money is equal - the right investor can be a catalyst, while the wrong one can become an anchor.
Whatever you decide, make the choice deliberately, based on careful consideration of your specific circumstances, rather than succumbing to the pressure of TechCrunch headlines or peer validation. Your funding strategy should serve your business ambitions and personal goals - not the other way around.
🤖 AI in fundraising
Fundraising is time-intensive and distracts from what matters - building the business. Emerging AI tools will help you save time whether summarising investor requests, preparing for meetings, or managing due diligence materials.
Here are a couple of tools that have been a game changer for me recently:
NotebookLM from Google is the best tool I've seen for retrieving key information from documents and summarising notes. If you're a podcast nerd like me, the tool can even convert a boring report you need to read into a two-expert conversation that is far easier to take in. If you haven't already, try it here.
Humble AI is a great tool to build your own mini personal assistants. With Humble could save you a list of web pages or LinkedIn profiles you're visiting as you go, scrape the speakers for your next event, and much more. Explore here.
📖 Interesting things I’ve been reading….
AI Investment Trends 2025: Beyond the Bubble
J.P. Morgan Asset Management discusses the evolving landscape of AI investments in 2025. The article emphasizes that while megacap tech stocks have dominated the AI narrative, there's a growing shift towards identifying opportunities beyond these giants. Investors are encouraged to explore sectors where AI integration is emerging, potentially offering more attractive valuations and growth prospects. This diversification reflects a maturing AI investment environment, moving past the initial hype and seeking sustainable, long-term value. Read more.
Venture Capital Trends 2025: What's Changing & Why It Matters
Waveup's blog delves into the significant shifts in venture capital strategies for 2025. Key takeaways include a heightened focus on capital efficiency, with investors prioritizing startups that demonstrate sustainable growth and clear paths to profitability. There's also an increased interest in deep tech sectors, such as AI and biotech, where groundbreaking innovations are reshaping industries. Additionally, the article highlights the importance of geopolitical factors and regulatory environments in influencing investment decisions, signaling a more holistic approach to venture investing. Read more.
Top Venture Capital Trends to Watch For in 2025
GoingVC outlines the prominent trends shaping the venture capital landscape in 2025. The article notes a resurgence in IPO activity, providing more exit opportunities for investors. There's a noticeable shift towards investing in startups that align with environmental, social, and governance (ESG) criteria, reflecting a broader commitment to responsible investing. Furthermore, the piece discusses the rise of alternative funding models, including revenue-based financing and rolling funds, offering startups diverse avenues to secure capital. Read more.
About Raise Like a Pro
Raising a funding round isn’t rocket science. It’s not even brain surgery. But it's incredibly time-consuming, HARD and emotionally challenging.
As a founder, your time is better spent building product, finding product-market fit, signing up customers, and building your team. Yet fundraising demands an enormous amount of your attention and energy.
I've witnessed countless founders struggle with this balance. They get stuck in the cycle of endless pitch meetings, confusing feedback, and the dreaded "no's" that seem to pile up without explanation. Even successful companies like Canva, now valued at $25.5 billion, started with their CEO Melanie Perkins hearing "no" over 100 times before getting that crucial first "yes."
I'm going to share my exact playbook – the same one I use to raise millions for startups across the world. This isn't about theory or inspiration. Instead, you'll get:
The actual processes I use to close deals.
Step-by-step morning routines for effective fundraising.
Real email templates that get responses.
Meeting scripts that convert to term sheets.
Pipeline management techniques that close deals.
The stuff you really need to know so you don’t get screwed by investors.
My days are spent navigating negotiations with every type of investor: angels looking for their next big win, syndicates pooling capital for bigger deals, and VC firms conducting thorough due diligence.
I'll share insights from all these perspectives, helping you understand how each type of investor thinks and what they're really looking for.
What's coming up
In the next issues, we'll dive into a whole bunch of stuff including:
How to structure your fundraising for maximum efficiency
The exact outreach strategies I use to get investor meetings
Common terms to watch out for (and how to negotiate them)
Ways to create competitive tension in your raise
Due diligence preparation that speeds up closing
Raise like a Pro is what David Levine does every single day though this business Glenluna Ventures. An exited founder, he raises money each and every day for founders all over the world from investors all over the world.