My First Nine Months as a Founder

This post is inspired by Ben Yoskovitz’s “My First 9 Months as an Angel Investor”. Ben is a trusted advisor and angel investor in sendwithus.

I think it’s really important as a startup founder to be both introspective, and analytical. I’m self-aware enough to recognize that a) I’m new at this, and b) I need to learn quickly. For me, the best way to accomplish that is to pay very close attention to what works and what doesn’t, and be brutally honest with myself about the results.

This post describes some of the things I’ve observed and learned during my first nine months as a founder. It’s in no way intended to be instructive, or advisory.

1) Founders get a lot of advice. I know everyone says you’re “supposed” to treat all advice as independent data points, but that’s easier said than done. Being critical of advice is something I’ve had to learn pretty quickly, and I’m still not great at it. There was a particular moment, very early on, when an advisor told my co-founder and I that we agreed with him too much, and that it made him nervous. That really stuck with me, and I’ve tried to be overly critical of advice ever since.

2) Raising money is addictive, and thus dangerous. There’s something inherently thrilling about lining up a perfect day of meetings with “A-list” investors. Investors you’ve read articles about, or follow on Twitter. It’s all a bit surreal to walk into the coffee shop and shake hands with someone you’ve read about for years. The feeling is addictive, but also dangerous. Taking meetings and working term sheets can feel like progress, when in reality, you’re doing very little to actually grow your company.

3) I’ve never made a pitch deck. Don’t get me wrong, I think a well crafted pitch deck can be a beautiful thing. But we haven’t had to make one yet, and don’t really plan on it. I think investor relations should be two-way, and it’s important to me to have actual conversations with anyone interested in helping us out. In fact I’d go so far to say (and often do) that I’m not interested in working with anyone who’d disregard (or fund) a startup based on deck alone. But maybe I’m naive about this. Maybe decks are the natural evolution of high-volume deal flow.

4) Nothing compares to meeting in person. I find this applies to most relationships: customers, investors, employees, etc. All of our important sales and partnerships have happened in person, and all of our big technical challenges have been overcome by getting the team together around a whiteboard. In this regard, I’ve learned to be willing to travel on very short notice — it’s almost always worth it. This aspect of business is pretty new to me. As a young coder, I always dreamed of sitting in a coffee shop, hacking on a laptop, while millions of customers paid for my product. But that’s just not how it works.

5) Writing code is comfortable, and thus dangerous. As a technical founder, this is something I struggle with. When I want to relax, I write code. But I know deep down that writing code is never going to grow my company, and I’ve learned to become incredibly aware of the amount of time I spend doing it. As a general rule, I try to complete the uncomfortable tasks first, and treat coding only as a reward. Being disciplined about this can be tiring, although having a second technical founder who “gets it” can help a lot.

6) Sales tools are complicated for a reason. When we first launched, the ability to track leads and opportunities was useless and confusing. In hindsight, I realize that’s because we had no idea how to define a “lead” or “opportunity” for our business. But early on, we ignorantly thought it was salesforce’s fault and we rigorously tested various competitors. As our sales process developed, salesforce started to make sense — not because we learned how to operate it, but because we learned how to sell our product and track the results. Even now, we have frequent “lightbulb” moments where a salesforce feature will suddenly start making sense.

7) Real company culture is organic. Or at least it should be. To me, company culture is how you react when a server goes down. Or a big customer signs up. Or when the team pulls together to push a feature 48 hours faster than anyone thought it could be done. It can’t be manufactured, or enforced — it’s something every team member must work towards, and it starts with the founders. But again, maybe I’m naive and all that changes at employee fifty, or even fifteen.

8) I have no idea what I’m doing, but I think that’s ok. Everything we do is an experiment, and the goal is always to record and learn. Learn what works, learn what doesn’t, and constantly be evaluating, prioritizing, and improving. It’s very hard to know beforehand what matters and what doesn’t, and being disciplined enough to always question what’s important can be challenging.

sendwithus is my first “real” startup, although I’ve had several entrepreneurial projects leading up to it. We started in October 2012, founded in January 2013, and went live with customers in March 2013.

So like I said, I’m still pretty new at this. Personally, I’m curious to see what I think about this post in another nine months.

Proud dad, husband, programmer, DM, and Canadian. Building a wonderfully unique developer community.

Proud dad, husband, programmer, DM, and Canadian. Building a wonderfully unique developer community.