James Sherwin-Smith of Growth Street and Tom Valentine of Secret Escapes talk raising capital and funding rounds, in episode 3 of our Founder to Founder series.

Any scaling, fast-growth digital business must at some stage come to terms with selling a slice of their business in exchange for funding. Here’s the bad part: Tom says it never feels easier.

Growth Street, at the time of filming, had just come off the back of a $8 million funding round, whilst Secret Escapes, through Series A, B and C have raised £73 million. However big your business gets, you can still feel very small sitting across from these investors, and it can feel like a job interview. Both Tom and James say that the more experience you have in those meetings the better.

Leaning on their experiences, and sharing their stories at different stages of the game, Tom and James give their brutally honest views on the big lessons they learned from raising funding. What they are sure to consider before they enter into another round?

They also discuss the things you might not normally consider when planning a raise, like the involvement of the team back at the office when you’re out on the funding road. Prefer to listen as a podcast?

Our Founder to Founder series explores the challenges entrepreneurs face with five interviews between members of our Future Fifty and Upscale programmes.

Watch episode one – Asi Sharabi and Alex Klein: Going Global

Watch episode two – Matt Buckland and Anoop Unadkat: Recruitment

Keep an eye on our social channels for updates and tune in again for episode four.