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Episode Drop
#106 Dotcal: The Calendar Wars is stirring up excitement among listeners and investors. Meet Dotcal - your new favorite scheduling tool.
Vol. 1 Issue 7
Let me tell you a story about David Matthews.
When we chose David to be on The Pitch Josh said, "This guy is gonna nail it. He is one of the best fundraisers I’ve seen."
It’s true. David was extremely well prepared. But he arrived at the studio with a major case of anxiety. The pressure of fundraising is no joke.
So we gave him tequila shots and invited him to meet the investors… BEFORE his pitch. This is not the typical order of events.
You can see in the videos David reads his pitch from his phone because he’s so nervous.
This guy is amazing at fundraising! And he had a panic attack before his pitch.
The entrepreneurial journey is not for the faint of heart. Last fall while fundraising for The Pitch, my Apple Watch notified me of an "increased resting heart rate." I was not coping well.
These are not isolated cases. Many of you could tell me your own stories of anxiety, depression, and panic attacks.
Through my own struggles with anxiety, I eventually discovered the underlying issue: control. The source of anxiety is lack of control.
As much as we want to, we cannot control everything. The world was slapped in the face with that fact when Covid came on the scene. Everyone realized we have way less control than we think. And mental health spiraled.
As founders, CEOs, and decision-makers, it may seem like we have all the control in the room. But when you step in front of an investor and ask for money you realize they hold the power to make or break your business.
Anxiety and hopelessness can easily slip in when we realize we don't have the power to ensure success.
But…
I think there is so much power in simply recognizing the problem.
Problem: “I don't have control over the investor’s decision.”
Solution: Determine where you have control.
“I can control my pitch and craft it specific to each investor.”
“I can control my sleep, my rest, my food, my exercise...”
The goal isn't to become obsessive about finding things to control - that leads to more disorder. The goal is to have realistic expectations of what you can control and what you can't.
Ultimately, you do your best and release the rest. That has to be enough. You can't control anyone else.
There will still be difficult moments, but you can choose to look for gifts in the hard times. In David’s case it was human connection.
In the midst of David’s anxiety, Josh and I tried whatever we could to help - I’m not sure if tequila was the right move, but you work with what you've got!
In the end, the experience of going through something intense together - and dealing with it together - strengthened our relationship in a big way.
David came in as an acquaintance. He walked out as a friend.
In summary:
You’re not alone if you’re a founder experiencing anxiety.
Determine what you can control and release the rest.
You will still have hard moments. That’s okay. Choose to find the gifts in those moments.
Dotcal Asks
We need everyone to start building their Dotcal scheduling networks! With this in mind, our #1 ask is to share Dotcal with those who could use it and/or invite others to your Dotcal network to kick off network effects.
Shout outs on social media -- we want to angle ourselves more as a scheduling network and less as a place to make pretty booking pages (though we'll always be good at that too) Find Dotcal on Twitter, Instagram, LinkedIn, and Facebook.
The Pitch Deals
Open deals from The Pitch Syndicate. Click the link to apply:
Tether - Officially a Delaware C-corp! Can I get a hallelujah?! (Listen to Ep. #102)
Dressd - The Red Ocean doesn’t scare everyone. (Listen to Ep. #104)
Dotcal - Ya’ll started applying to the fund like crazy after this episode! (Listen to Ep. #106)
Or invest in them all through The Pitch Fund!
Coming Up Next
Next week’s founder is looking to find a problem for his solution… Yes, you read that right. (Episodes drop Wednesday. The Pitch Insider publishes Fridays. Follow The Pitch wherever you get your podcasts.)
On Social
Video clips from all of Season 9, including Dotcal, are on Tik Tok, Instagram, Twitter, LinkedIn, and YouTube. Help us get to 1,000 followers on Tik Tok so we can put our link in the bio.


Love the newsletter Lisa! Great job as well with the tequila shots 😎
Hi. I don't understand why the investor in DotCal, Willem van der Bosch with Soma Capital, would encourage people to invest in Dot Cal. With more investors, doesn't that just dilute Soma's investment?