Hindsight Is 20/20… But Don’t Look Back

Hindsight Is 20/20… But Don’t Look Back

Simili has not launched yet, but (or should it be “and”?) I can think of so many things I would do differently if I could step back in time and do it all over again.

I do believe that everything happens for a reason, and that sometimes learning things the “hard way” is the best way, so I’m not really regretting my decisions – I just wanted to capture these “woulda/coulda/shoulda”s while the lessons are still fresh. I’m fairly certain that there will be a Startup #2 someday, and I’m hoping that my future self will heed my current self’s advice. I’m stubborn enough that I needed to try it MY way before all of the available startup wisdom could really sink in, but you’re probably smarter than I; maybe these lessons I’ve learned will help you, too.

So without further adieu, here are the five things I wish I’d done differently, both macro and micro:

  • Talk to a lot more people, a lot sooner.

This means customer discovery, but it also means connecting with people who may be interested in what you’re working on. They may be able to help – or even get involved in a more longterm way – and it’s easier to truly share the dream (and/or find a co-founder) when nothing is built yet.

  • Be leaner.

I had a first web-based prototype built too early. This was in part because I am shy (and stubborn) and didn’t want to talk to customers, and in part because I convinced myself that as a person who was employed full-time, I had more money than time to spend validating this idea, so I went for it. That was probably not wise.

  • Be a learner.

Fortunately, I really love learning, so this one is coming pretty naturally – and I’d guess that by definition, anyone who is an entrepreneur is always learning. That being said, given that I’m trying to build a mobile app, I wish I’d been less intimidated by things like “tech stacks” and “databases” and just jumped in to learning about technology head-first, rather than wading in bit by bit.

I initially thought that my time would best be spent leveraging my area of strength – marketing and branding – but there’s SO MUCH more that has to happen to get something off the ground, and when you look around and realize that you’re the person who has to do it, there’s only one option. Learn.

  • Get organized.

It’s always easier to START organized and STAY that way than it is to go back and clean things up. You’ve got a STARTup, so take this opportunity to keep things organized from the beginning. This means files on your computer, receipts for purchases, task management systems, etc.

It’s tempting to think that this is not important and that you should just be focusing on the almighty product (and you should!), but in my opinion, an “ounce of prevention = a pound of cure” here. You’ll be juggling a lot, so try to put a supportive infrastructure in place as you go.

  • Know what you (and your family, if you have one) are signing up for.

I thought I was just scratching an itch. I figured this would be a one or two year thing, and then I’d move on to focus on my career in naming. Wrong. First of all, Simili is probably not going to take off that fast. Secondly, I’ve discovered that scratching the entrepreneurial itch doesn’t make it go away; at least for me, it makes the itch stronger.

I knew this was going to be hard. I didn’t realize HOW hard.

I knew there would be financial uncertainty. I didn’t fully appreciate how much, or what that would feel like.

Because I didn’t know all of these things, I didn’t adequately communicate with my husband about what he could expect. The very nature of a startup is that it’s unpredictable, but I think I could have done a better job of anticipating some of this. I’m lucky in that my husband is totally and amazingly supportive, and we’re figuring it out as we go. Seriously, though, there should be an “entrepreneur spouse support group” or something.

Good luck, everyone!

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