Five things I learned fundraising as a first-time founder

Earlier this year, I raised a pre-seed round for my company, Arrange, a platform that makes it easy to add reminders and to-dos to your calendar. I’m a first-time founder, it was my first time fundraising, and it all took place over Zoom. I wrote about the fundraising process and how I went about it over here. 

This post is meant to capture something else – namely, how wrong some of my assumptions were going into fundraising and what I learned along the way. Here are 5 surprising things I learned while fundraising for Arrange:

1. I was terrible at predicting investors’ behavior.

I ran a pretty intentional fundraising process, and spent a lot of time researching firms and partners and identifying the best person in my network to make a warm intro where possible. So based on any given firm’s investment stage and thesis, as well as the strength of the mutual connection/introduction, I felt confident in my ability to predict which investors would be the most interested in me and in Arrange. I couldn’t have been more wrong. There were pre-seed firms with strong mutual connections that I thought would be slam-dunk convos who turned down an email intro. And there were big, well-known, usually-later-stage firms with less-strong intros that moved really quickly. (In fact, I almost didn’t pursue Arrange’s largest investor because another founder swore they “wouldn’t touch” a company this early). The lesson here? Check your assumptions and shoot your shot since you never know how people will respond.

2. I got very little pushback on being a solo founder.  

The overwhelming consensus view in Silicon Valley is that two founders are better than one, and that tech startups in particular need a technical cofounder to be viable. The truth is that being a solo founder hardly ever came up as an issue at my stage. Of all the investors I met with, only two cited lack of a technical founder as a reason for passing on Arrange, and both investors were technical themselves. On the other end of the spectrum, one well-known investor went so far as to tell me he “loves solo founders.” The moral of the story? Don’t treat finding a cofounder as a box to check before you start fundraising. Cofounder (and investor!) relationships are like marriages, and having no partner is better than having one (or worse yet, the wrong one) solely for the sake of doing so. 

3. I never had any success with cold outreach.

This one bums me out to even write since I had the privilege of having warm intros to many of the investors on my target list. But the truth is that I did not raise a single dollar from people or firms that I reached out to directly. This included angel investors who advertise open DMs on Twitter, and even a VC firm that had once targeted me(!) in their cold founder outreach. I don’t take any of it personally, but I couldn’t help but feel disappointed that, from what I can tell, VC is still a relationship business. So, if you’re a first-time founder, my overwhelming advice would be to invest in building relationships with investors and/or people who can open doors for you however possible.

4. I didn’t encounter a single bad actor. 

I’ll be honest: I entered the fundraising process cautiously optimistic, but also prepared for the worst. There are tons of horror stories about pulled term sheets, predatory terms, and more. I’m happy to report that this was not my experience at all – in fact, I loved fundraising. The worst I encountered was an awkward call or two, but the vast majority were enjoyable. A few investors ghosted me, and others took a long time to say no, but in no case did they mean any harm – people are just busy or unorganized (or both). 

5. I really enjoyed the process. 

I enjoyed fundraising a lot more than I thought I would. I didn’t expect to hate it – I like sales – but I managed my expectations and didn’t anticipate feeling strongly about it one way or the other. What I failed to appreciate is how much I’d enjoy meeting and having interesting conversations with so many smart people, many of which I still think about. Overall, fundraising exceeded my expectations, and not just because I was happy with the outcome.

It’s worth noting that this was my personal experience, and surely others have had different (and harder) ones. But overall, the fundraising process exceeded my expectations, even if some of my assumptions turned out to be wrong. If you’re embarking on a fundraise for the first time, hopefully this was helpful.

Interested in learning more about Arrange? Join our beta here and check out our open roles here.