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Written by: Marc Halpin


There’s a boxing ring in the gym I go to. 

Quite often, there are people in the ring. They sometimes have their hands taped up and they have their gloves on. They shadow box and the trainer puts on punching mitts and they try to hit them. “1, 2”… “1, 2, 1”. 

You know how it goes. It’s all very energetic!

There’s a handful that seem really good, they have all the gear as well, you know, the ‘Title’ stuff and those high boxing boots. I suspect they would fancy themselves in a real fight should the opportunity arise.

I imagine them having a plan on how to win in a street fight. Maybe they’ll lead with their jab, then use that uppercut in some great combo they rehearsed with their trainer and his mitts. 

It’ll be a great plan, like a really great plan and it will work super well right up until ……they get punched really hard in the mouth!

“Everyone has a plan ‘til they get punched in the mouth” – Mike Tyson

Fundraising may not have the physicality of a boxing match, but after all the planning and preparation, the deck and the data room, the outreach and the practice, that first meeting may well feel like a figurative punch in the mouth! Oh, and then comes the second and then the third….

Those punches are most often the doubt, the challenges, and of course, the ‘no’s’. Clearly, it’s a  mental battle, but a battle it is!

In the beginning, it’s very exciting – maybe a little scary, but that’s it. In the end, you have a multi-million dollar check and stories to last a lifetime. But in the middle, the punches just keep on coming!

Wondering how to handle yourself in this particular fight… a way to maybe deal with the punches?

 Here are five strategies that may help:


  • They’re jabs, not knock-out punches. It actually helps to enter this particular sport realizing that it is somewhat of a numbers game. Psychologically understanding this from the get-go will really be helpful. No’s are simply part of the process, you’re going to get more of them than yes’s and that’s just fine.

  • Always grow your roster. Research, connect, and seek support. Think of building your VC list as a team sport, get help! It’s way better to have an ever-growing list and know you have more opportunities to get to a yes. Always keep growing your list.

  • Spend time with a coach or two. Everyone who has raised venture capital has a story to tell, trust me! Listen to their stories, hear about how they navigated the process, and practice with them, then practice some more!

  • Do the gym work. It’s business after all! Know your revenue history, know your forecast, be ready to explain your use of funds, build a great deck and more…. Get some help critiquing all your numbers. Be exceptionally good at this.

  • Try and enjoy the journey. Yes, it’s tough but try and look at this as an opportunity. In this sport, you’re actually going to meet some great people and some are going to be business partners and friends for a long time. Keep smiling and keep swinging.


Finally, I’ll hand it back to a guy that knows…

“As long as we persevere and endure we can get anything we want” – Mike Tyson


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