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Facing Every Founder's Worst Nightmare

Jason Yeh
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October 10, 2023
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Tiffany Kelly on Funded

Insights from Tiffany Kelly

Last week I released the season finale for my podcast Funded, where I bring on founders to tell their stories of how they raised millions. Believe me when I tell you we went out with a bang.

For this episode I brought on one of the grittiest founders I know - Tiffany Kelly, founder and CEO of Curastory. I was always impressed by her motivation and drive, but after this episode and having learned a lot more about her backstory it all makes perfect sense.

I met Tiffany while she was in the process of preparing to go out and raise her seed round which was… rocky at first. But thanks to her determination and the help of a friendly VC, she ended up getting the guidance she needed and closing a pretty solid round. Yay for helpful VCs!

Fast forward to now where she just closed her Series A, but not without a challenge. Keep in mind, she started going out to raise around the same time as the SVB crash - how fun. But to her surprise, she found a lead investor early on. Things were running smoothly (almost too smooth). But then she received a call: one of the firms who already executed a term sheet said they wanted to change the terms. Needless to say her world got flipped upside down and some hard decisions had to be made. I'll save more of the details for the episode 🤫.

Now for the takeaways...

Keep running a process until that money is in the bank.

I see this happen time and time again. A firm shows interest in your round, maybe even executes a term sheets(like in Tiffany's case) and out of excitement the founder drops everything in order to close the deal. Next thing you know the firm gets cold feet and the doors to your other leads are now closed. The number one thing I emphasize in my teachings around fundraising is this idea of continuing to run a process. What does that look like?

"Interested? Great. We are going to continue running our process and speaking to other firms. You can let us know if you'd like to move forward and as long as a spot is still available, we'd love to have you join."

Don’t put investors on a pedestal. Placing the authority back in your hands so that you don't get walked over. Stop chasing.

Set yourself up for success

I am a firm believer in learning by messing up and falling down. But I also believe if you could lessen the fall, why wouldn't you? Fundraising is an entirely new world for most founders. Even if you've raised before the landscape is always changing. That's why I always emphasize the importance of fundraising prep. That means... educating yourself on investor psychology, creating a target list, preparing your emails, crafting your narrative in a way that's digestible for VCs, the list goes on.

The preparation you do before your fundraise will reflect directly in your confidence levels around investors. The more prepared you are the more confidence you will exude. The more confidence you exude the more interest investors will have in you. And if you can back that confidence up with proof on how your company WILL hit that next level with the help of some capital, you're golden.

If you're serious about your company's success, you'll do the work. I guarantee after the experience Tiffany had, she's going to run her process a whole lot differently for her next fundraise.

Tiffany was kind enough to openly talk about some of the serious lessons she had to learn for raising this round. I highly suggest you take the time to give it a listen so you know what to avoid and how to bounce back if all goes to shit.

I hope you enjoyed this breakdown.

If you're looking to listen to the full episode, click here.

If you're looking to watch the full episode, click here.

If you're looking to learn more about Tiffany or Curastory, look below:

Listen to the full episode here:

Tiffany Kelly

Curastory

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