Day 09 — The Good, the Bad, and the Ugly

The truth behind why starting a company is hard

Bob Weishar
5 min readDec 9, 2020

“Starting a company is hard” is a phrase that leaks into startup lexicon all the time. But for the first 6 months of Invincible, I really just didn’t get it. As a founder, I literally get to wake up every morning and build my future — however I want.

But the longer you continue in a startup, the more you start to come around to the idea. Maybe it’s just burnout sneaking in, or maybe starting a company just is actually just hard.

But I think there’s more to it. Yes, no doubt starting a company is hard. But overcoming challenges is also what makes the journey worth it. Plus if it were easy, everyone would do it.

But why is starting a company hard? The way I see it, the phrase needs to be broken down:

  • The Good: Talking to users and building a product that solves real challenges is hard. Finding product market fit is really hard. But these activities can also be really fun, and if the messy creative journey isn’t something you enjoy, you should probably stay away from starting a company.
  • The Bad: Dealing with all the “business” aspects of starting a business — like accounting, taxes, insurance — is annoying. But it’s the price of entry to run a company, and luckily, they’re all completely manageable mainly through 3rd party software tools.
  • The Ugly: Sacrificing your personal life and losing the big-company benefits you took for granted sucks. To me, this is by far the hardest part. Leaving a paying job has a massive opportunity cost — on relationships and comfort — but it’s the sacrifice you must be willing to make.

Here was my good, bad, and ugly day of work today.

The Good

1. Responding to Families for Interviews

I started the day by responding to the families that I reached out to last night on Instagram. So far I heard back from 5 of the 10 families I reached out to, and I scheduled 3 of 5 interviews I set as my goal for the week.

2. Update Training Modules

Knowing today would mostly be coordinating interviews, I set down the experiment and used today to clean up a bunch of work that’s been on my backlog.

The first of these is our training content in our app. I took a few hours to refresh content based on feedback I’ve received, such as response text (thanks, Steve!), image assets, and added a more gamified approach to the end of each module where kids can level-up with superhero powers.

Updating our Training Modules

3. Releasing New Product Features

Today we also pushed a really exciting app update: the ability to export data. It allows families to share data with their doctor, so that care can be improved and kids can have better outcomes. It also allows us to help school nurses save time on documentation, which today is all done on paper.

Invincible’s New Export Feature

Here’s what the app build process looks like:

Building our App in Expo

4. Updating our team website

I updated our team website to include our newest team member, Elizabeth! She’s been a huge part of our team these past 2 months and it’s been really exciting to see her learn quickly and deliver a ton of value.

Our website is built in Webflow, I highly recommend it for building great no-code websites.

The Bad: Stuff I Never Thought I’d have to do

1. State Tax Stuff

Since COVID, I’ve been living back in Indiana, so I needed to change my tax filings (it has the added benefit of 5–10% tax reduction, too!). But with it comes paperwork. Gusto is my tool of choice, but it still takes some hassle working with state agencies.

2. Bookkeeping & Tax Preparation

Accounting & Tax is another really “fun” aspect that comes along with running a business. Each month, I need to do a little cleanup and make sure everything is in order. Luckily, I use Bench Accounting for both, and I’ve been really happy with their service so far.

The Ugly

Legitimately the most stressful part of starting Invincible so far has been managing my healthcare. Some things are just better when you work for an employer. I’m grateful that I can access healthcare and kind of can afford it, but it’s not cheap, and it’s not easy, especially when out of pocket my medication would cost over $1K a month.

The realities of starting a company

One way I’ve saved money on healthcare has been to enroll in an ICHRA plan so that I can pay my premiums pre-tax.

What Now?

Now it’s time to get ready for another “hard” day tomorrow doing what I love to do (well…mostly).

See you tomorrow.

My goals for writing this series are to👇:

For the next 6 months, I plan to start building Invincible in public. What’s in it for you? Hopefully, mistakes you can avoid mixed with some good ideas and tools that can be useful to you. And for me? Getting back some accountability you lose when you become your own boss.



Bob Weishar

Founder at Invincible, passionate about building healthcare products that inspire.