“If Only We Had __________.”

The deliberation and blame in the minds of SaaS founders — and how you can overcome it.

Life is tough as a small bootstrapped team.

You’re constantly playing the role of underdog, with few wins, little appreciation, and constant doubt.

There is never enough time, money, or energy to achieve what you want in the timeframe you want it.

So you start to look elsewhere. You subconsciously place blame on current teammates, events, etc. (or even the lack of future things).

If only we had one more developer, we’d be able to get to product-market fit faster.

If only we had a bit of funding, we could afford to try advertising and find our flywheel.

If only we had more time to focus on marketing, we could drive more consistent traffic and get more signups.

I constantly find myself thinking in terms of, “If only we had ______” and I’ve been trying my best to stop this.

The reality is that you can do all of these things, even with strapped resources, as long as you’re ok with it taking a bit longer.Which isn’t so bad.

“Take your time. Love your product. Love your customers.”
Jeff Berg, Owner of Planning Center Online

Avoiding the Rabbit Hole

The best thing you can do, is detect when you’re thinking this way.

Anxiety and fear of moving too slow seem to be triggers for placing blame on external factors.

When you’re experiencing these feelings, do a double-take.

Question your thoughts, and challenge yourself to prove their validity.

Setting Deliberate Roles and Goals

One response I’ve found to be successful, is to be deliberate about the roles and goals of teammates. This probably sounds super obvious — but as you know, founders have an immense range of tasks on their plates, and I know I need constant reminders to be deliberate about various aspects of my day.

It’s so easy to place tasks on auto-pilot as they become familiar, but that is one way quality decreases over time.

Similarly, by not being deliberate and clear about who should be working on what, and exactly what they should be delivering when, you are leaving the door open to be disappointed.

One of the worst aspects of your culture can be growing disappointment and resentment amongst teammates.

Beyond setting goals for your team, you need to set goals for your product and customers. This doesn’t mean you should open up Excel and spend hours creating a 5-year MRR “forecast.”Although that’s always fun!

Rather, you should look at the work you’re doing on your product, and how you’re trying to help your customers be more successful…and set measurable goals to track progress.

So take a day, grab a pen, and do some planning.

Work with your team to make sure everyone is on the same page, and that you’re working in the same direction.

The milestones you decide on may not come as quick as you like, but that’s fine.

And this shouldn’t be a one-time thing. Planning should be a regular part of your flow, and an easy fallback whenever you start feeling anxious.

Do You Actually Need Help?

At this stage, you should have a good idea of whether your internal frustrations are justified, and whether you actually need help…whether that’s in the form of hiring someone else, raising some funding, or another form of outside assistance.

Based on your deliberate planning, you’ll have a roadmap that either:

  1. Calms you and puts things in perspective, or:
  2. Helps you be objective about what’s actually needed

In the case that you do need outside help, consider how you could re-arrange your roadmap to shift revenue-building activities sooner. Can you find a way to continue self-funding and grow faster by making sacrifices in less-important areas of your business or product?

I’m Matt Goldman. I spend my days building awesomeness into HookFeed (Customer Analytics for Stripe). I also interview startup founders like Hiten Shah and Adii Pienaar twice a week.