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This week's newsletter features an exciting Q&A with Esther Crawford, co-founder and CEO of Squad, where she details her story of building and growing her startup for four years then choosing to sell it to Twitter instead of raising a Series A. Below, we share only part of Squad’s story with Esther; read the full interview on our blog.

We also update you on last week's Pitch Deck Interest metrics, a post from Russ Heddleston on raising a Series A, and pitch deck trends we're seeing in the DocSend Fundraising Network now that we have over 1,000 deck applicants.

Q&A with Esther Crawford

Esther Crawford is the co-founder and CEO of Squad, a social screen sharing app, that she recently sold to Twitter after building and growing it for four years.

Read the full Q&A to learn how Squad started as something completely different, dig into the full fundraising timeline, and more on DocSend's blog.

Over the past 4 years, you have launched multiple versions of your company and have raised multiple rounds. On a high level, can you share any context around the major events in the timeline above?

Esther: From the beginning we stayed really lean as a team so that we could be nimble as we built and learned from customers. When we started the company it was an ambitious and audacious goal -- build a new social experience in the midst of an era where consumer social was decidedly not hot. But that’s where my passion has always lived, and I knew when it came to building social products that it might take a few tries to find the right fit. 

I wanted to work on solving the problem of loneliness through technology because it was the core problem I’d faced in my own life. Since I wasn’t married to a particular solution we launched a lot of small experimental products across a few platforms. 

I always felt it was better to work in public whenever possible -- so we launched several times, because, why not? I never felt precious about it. 

I was authentically excited by what we were building and felt it was useful to get additional feedback from the market whenever we could. 

As an early-stage venture-backed company, our market was always two-fold: our actual customers and potential/current investors. I tried to err on the side of sharing the latest & greatest to help bring industry insiders and investors along on our journey so they’d feel more connected to us. I know it helped because it kept us in the conversation.

Launches are important forcing functions. Stealth mode is rarely a good idea. 

Trust me, it’s way better for people to subtweet or shitpost about your startup than for them to be totally ambivalent to your existence. Indifference is death.

As a founder, fundraising takes a lot of time and effort for each round. In your experience, having raised multiple rounds for Squad, what are a few lessons you have learned that can help founders in their fundraising process?

Esther: Have a process. I think that’s it. 

The biggest mistake I made at the beginning was setting up meetings with nearly any investor who would talk to me -- without a clear timeline or defined next steps to take. That’s a great way to waste your time.

The only way to get a deal done is momentum. The job of the CEO is to create and then continue to nurture the momentum in a deal process, and the only way to do that is by setting up guard rails, deadlines, and creating external pressure. 

Founders often forget that they are in control. VCs are lucky to invest in founders, not the other way around. All the best VCs know that, which is why they’ll pull crazy stunts to give amazing founders lots of money.

Read the full Q&A with Esther Crawford on DocSend's blog

In the full Q&A, Esther digs into Squad's full fundraising timeline, how her team was able to pivot from a product that just wasn't working to one that went viral from the start, and why she chose to sell Squad to Twitter instead of raising a Series A.

Pitch Deck Interest Metrics Update

Investor time spent reading is now below the three-minute threshold, where they’ve been for most of the second half of 2020. Even though investor interest seems to have begun its end-of-year decline, activity is still 20.5% higher than at the same point in 2019. Founder links created rose by 13.43%. (retweet our tweet)

Read our analysis of last week's fundraising marketplace activity.

Recommended Reads

Startup Fundraising Trends from the DocSend Fundraising Network

We did a little investigating into the decks that came into the DocSend Fundraising Network during Q3. Let’s find out more about what kinds of teams have been raising money, where they’re from, and what kinds of spaces they’re innovating in.

Read the full post on DocSend's blog

Pitching In The Big Leagues: An Inside Look At Series A Fundraising

The Series A round has become a serious milestone for startups. Based on real-life investor and founder data from our Series A report, Russ Heddleston, CEO of DocSend, details three main takeaways to consider before you start your Series A fundraise.

Read the full post on the Entrepreneur's Handbook

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Listen to Funded on your favorite podcast app!

The Funded podcast features some of the entrepreneurs you’ve always admired to tell a story you haven’t heard before — how they raised millions in venture capital. You can listen to the first 3 episodes right now and get the next one on Tuesday.

Subscribe to Funded on Apple Podcasts, Spotify, or search "Funded"

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