The Story Behind Language I/O's $8M Series A + Fundraising Fieldnotes 2.6.24

Featuring Heather Shoemaker, Founder & CEO of Language I/O

Author

Jason Yeh
February 06, 2024

Before we get to this week's post...

If you’re a SaaS founder preparing for a fundraise in 2024, join us on 2/21.

This free event will help you stay ahead of emerging trends in the venture capital landscape as we lead a discussion and open Q&A with industry experts from Carta and leading VC firms.

Specifically we'll cover:

  • The metrics that matter most in fundraising for SaaS

  • ​Things VCs look for in SaaS investment opportunities

  • ​What it means to be a “venture-backable founder”

  • ​Hot markets, venture-scale markets, and everything in between​

… and now on to this week’s post

A few months ago, I got to talk to Heather Shoemaker; a VC-backed founder who's raised over $20M in venture capital for her translation software company, Language I/O.

Two weeks ago, her interview dropped on Funded where she got to share her story behind her earlier rounds and how that ultimately led her to close Language I/O's $8M Series A in July of 2023. It's an episode worth listening to - especially if you're a female founder in the tech industry.

I did want to share with you some of my favorite takeaways from the episode, so let's get into them.

Rejection is a part of fundraising

"You just have to have really thick skin and the ability to, at the end of the day after you've had these really depressing conversations, just remind yourself that that's just one person."

This one's big. Heather went through a good year of getting rejected by investors before she was able to make any progress. Part of that was because investors didn't like that she was a female in the tech space, the other part was that she didn't know much about fundraising, and the last part was that VCs were having a hard time understanding her unique insight.

Add all of those together and you're bound to be let down - a lot. The same goes for most people going out to fundraise. You will be let down - a lot. That's part of it.

The truth is, most founders don't allow themselves to get let down enough. I've talked to so many founders who got rejected 100+ times before they got the big 'yes' that led them to close their round.

Don't let rejection stop you from continuing your process. If anything, let it fuel you.

Shift your mindset: each no only brings you a step closer to your yes. Believe it and see what happens.

Prepare for doubts and misconceptions

"There were folks I'd start talking to and they would be like, 'Why did you try to grow organically? Like, the fact that you never raised money for the first couple of years indicates that nobody wanted to invest in you.'

Well, I wasn't trying, you know."

When Heather touched on this I gotta admit, I was surprised VCs were so stuck on it.

To give you a quick backstory, Heather never thought she would become venture-backed. Her company was already profitable, they were steadily growing, and there was no reason to. But as we know - things change. Competitors come, and there are things you have to do to keep moving forward. In Heather's case that meant going out to raise her first venture round.

The takeaway I have for you here is that VCs will sometimes ask you questions that make no sense to you. You will have to deal with a ton of misconceptions and doubts.

What I'd recommend you do is to write out a list of every possible question or misconception a VC might try to throw at you and create a solid answer to give them so that if they do bring it up, you are well-prepared.

It's a VC’s job to test you, make sure you do your studying.

Alright, those were the two takeaways I wanted to touch on but there are a ton more in the actual episode itself. If you want to:

  • Hear what it was like raising earlier rounds of capital

  • Hear the story behind Language I/Os $8M Series A

  • Hear from two of Language I/Os investors on why they chose Heather (great bonus!)

Make sure to listen to the full episode. I'll leave the links below!

Be chased,
Jason

Listen to the full episode here:
Language I/O
Heather Shoemaker

*If you have any suggestions on who we should interview or what we should cover in any of our shows this season, please reply and let us know!

And finally, we'd love to see you subscribe and leave a review wherever you listen to podcasts.

Thanks and happy listening!

It's tempting to want to show the world (VCs, peers, etc) how tough you are. Don't do that. Rest. Recharge. And don't pretend like it doesn't hurt.

Ha. From someone who has read many updates and written updates as a CEO... it's totally true. But remember that it's correlation not causation

“OK sure, but remember that time when…”

Small asks!

If you thought this was helpful or enjoyable in any way, I’d love for you to:

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  • Are you planning to fundraise? Join the waitlist for Fundraise with Confidence - the fundraising accelerator program that's helped founders raise over $250M 💰

  • Listen with a friend to Funded, my podcast that tells the rollercoaster stories of how founders raised millions (and subscribe🙏)

  • Ask me your fundraising questions so I can help you and cover them in a future issue

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