Lesson #4+: assorted collection of tactical things
a rolling compendium of notes and things I wish I knew
It’s been a while since I posted here – almost exactly 3 months to the day. I realize that I often have snippets of startup-related thoughts that deserve to make their way into a post, but are either too fleeting or random. Moving forward, I’m going to use this post as a rolling log of these types of thoughts.
In no particular order:
10/29/2022
Start with the low-to-mid level people for customer discovery; switch to the decision maker when pitching.
When pitching potential customers for commitments (e.g. LOI, co-develop agreement, or better yet, actual revenue), go directly to the buyer. Start your customer discovery with lower-level folks to gather feedback, hone your hypotheses, and learn to speak the language. But when you know you’re onto something and are starting to build, go to the directors and VPs.
I spent a lot of time trying to pitch to individual contributors who clearly had the pain point, but there was a noticeable tension and awkwardness on the calls because they had to convince their boss, or their boss’ boss, to talk to some random dude. This clicked for me the first time I talked with a VP who clearly had decision-making power. The a-ha moment was when I asked if they needed to loop in their legal team for an NDA, and they said that they’re able to share their standard NDA template directly. Talk about moving quickly.
In the customer discovery phase, work on ideas in parallel
Caveat that when you progress to the phase of building an MVP, it’s better to focus solely on building. But in the customer discovery phase, especially if you’re working on the startup full-time, there are a lot of rate limiters that are out of your control. Cold email response rates are low, calls take time to set up, and pouring in more time sometimes won’t get you results faster. I felt a lot of pressure to get results when things were moving slowly, and felt a lot better when I started working on a secondary idea in parallel. Unclear what the optimal number is — I’m convinced 1 is too few and 3 felt like too many, so I settled on 2, but YMMV.
Send monthly updates to advisors/investor/startup friends
I first got this advice months ago from a fellow founder friend. When they brought it up, I thought it sounded like an awesome idea for keeping friends up to date and holding yourself accountable…and then promptly forgot about it for months.
'I’ve sent a few updates so far, and it’s been one of my best decisions in the startup journey, for a number of reasons:
It’s helpful for yourself to reflect on what you worked on and to hold yourself accountable. There’s a clear log of: what was my goal and did I hit it, what went well, what didn’t go well, what are my goals for the next phase, etc.
It’s a low friction way to keep people in the loop. Most people want to help, but it feels awkward to text or email them. This makes sharing an update the default state, which reduces activation energy.
It helps others help you. I include a section at the end with 1-2 specific “asks” — things like intros or things I’m trying to figure out — and I’m always surprised at how many people reply. Most people are busy but want to help and see you succeed; this makes it easy for them.
It’s fun to keep in touch. Many of the people I’ve met along the way, I view as genuine friends. It’s always a dose of happiness to send out an update and see replies come in from people I like and want to keep in touch with.
Regarding cadence: I started out sending an update once every 2 weeks, and switched to once every month. I think either works. More frequent might make sense if you’re in the discovery phase and things are changing quickly; less frequent makes more sense once things are more settled.
11/15/2022
Underrated learning: thick skin
It sounds silly, but one of the biggest lessons I’ve learned in hindsight is to develop thick skin and shrug off negative feedback.
I stumbled across one of my customer call notes from a few months ago, where I received negative feedback, and it partially contributed to me disqualifying an idea. Knowing what I know now, I would have shrugged it off and continued.
This raises the hairy question of, what if I should have continued with some of the past ideas that I disqualified? Should I revisit them? I don’t have a good answer for this.
If I had to concretize this learning into a formula, it would be: focus on the yes’s, and in particular, the intensity of the yes’s. Ignore the yes rate (crude but I think you get the point). If you can get a small number of yes’s, even just one, that is an intense and committed yes, then this is enough reason to ignore all the no’s and continue pushing forward.
Love your insights!