My hardest lesson from fundraising? You probably don’t need to fundraise. Or at least as much as you thought you did. Fundraising itself is hugely distracting. And once you get a big raise done, now you have investors to manage, board meetings to prep for, and major decisions are now a negotiation. And if you raise money – trust me, you’ll find a way to spend it. After every raise, your monthly costs will step up. That’s fine if revenues rise nicely in line. But it’s a problem if something unexpected happens – and it normally does.
Nicholas Walters
President, SuperAwesome
– – – – –
Never stop fundraising. Always talk to investors—even just after closing a round—as these conversations can bring new clients, valuable connections, or future funding.
Early-stage VCs often lack deep technical expertise, particularly in niche areas like financial infrastructure. Corporate VCs tend to be risk-averse and slow; high-net-worth individuals with sector experience may be a better bet.
Raise before you need it. Extend your runway and never assume funding will remain accessible. If you have an opportunity to raise money from a position of strength, take it.
Create competition. Give VCs a clear deadline to deliver term sheets. Generate buzz and urgency.
Matthew Longhurst
Co-Founder & Chief Innovation Officer, Treasury Spring
– – – – –
Hard lessons learned:
1. There is a tradeoff in fundraising too early — You get the peace of mind of a paycheck (especially if you’re paying for childcare!) but you’re not building in the playful and private space of pre-fundraise.
2. Be intentional about what you want out of your cap table — We thought about this carefully and landed on a big brand for external signalling, a fund that specialises in and gets the funding stage we’re at, and a mix of experts in specific functions / regions / sectors including those of our likely ICP.
Mounir Mouawad
Co-Founder & CEO, Portia AI
– – – – –
One hard lesson is the importance of recognising signals early and adapting fast. In earlier rounds we slogged to meet as many investors as we could to find the one that gets it, but in hindsight, some common themes were clear from early feedback. We should have paused sooner, reflected, and adjusted strategy. Try to get a sense of what investors care about early on and have a hard look at whether the time is right or you need to prove something else and then come back to market. Fundraising is as much about momentum and timing as it is persistence.
Chris Eastwood
Co-Founder & CEO, Penfold
– – – – –
One of the key lessons I’ve learned fundraising $90m for Streetbees and Eloquent AI is that securing term sheets isn’t the difficult part—if your business is successful, you’ll likely be oversubscribed. The real challenge lies in choosing investors who truly understand your vision, stay supportive during turbulent times, and add tangible value beyond capital. The right partners accelerate your growth; the wrong ones can derail it.
Tugce Bulut
Co-Founder, Eloquent AI
– – – – –
Raising money can be very helpful if you have clear product market fit and a clear use of funds that you are relatively confident you can model outcomes too. But my advice is to be careful and have your eyes wide open. raising money is not a mark of success- growth and customer outcomes are. Keep in mind that once someone joins your cap table- they are there. And also be ready to fully take your eye off the ball of your day to day unless you are fielding off term sheets. All this to say do not give away your cap table or control until you atleast have a very confident stance on your product market fit.
Ryan Barry
CEO, Appcues
