Bootstrapped startups and the shit I learn in therapy

A reflection on the first 4 weeks at Krit during the COVID-19 pandemic

​Four weeks ago I wrote about putting one foot in front of the other.

I was trying to figure out what to say then—the right way to add my voice to the fray.

I’m still struggling to figure it out. So I’ll do what I did then and what I know how to do best: Share my personal experiences and feelings with you, and offer ideas on how they might apply to your life.

If you’re tired of reading about COVID-19, or just don’t want to read another think piece from a 26-year-old running his first business, feel free to skip this one. 🙂

Take time to catch your breath

For the first couple of weeks, it felt almost impossible to focus on anything other than the crisis. My anxiety was constantly heightened and our team felt the same. We weren’t as productive as usual, and pretending anything else was living in a fantasy land.

The partners and I gave our team some extra time off the first week to prepare for quarantine and to manage their anxiety. I didn’t feel like I could take the same time off that week, but I took a sick day a little bit later, and it made a huge difference.

Tips for your week:

Take some time to adjust and detach from work, and give your team time and space to adjust. Rest is hugely valuable. It may seem weird to take a day off when you’re already at home, but stepping away from work for an extra day really does make a difference.

Some weeks, as a leader, you simply can’t take time off. But busy weeks won’t last forever, and it’s worth the headspace to take a day off and rest as soon as you can.

Give back if you can

Another thing we did the first week was redirect some planned internal time to help two local food and bev companies get set up to handle online orders. We did it pro bono just to help the community in some way.

In truth, we did overstretch ourselves. We didn’t have time to plan the project well, and it put some stress on our team to figure things out as we went. But helping in some small way felt empowering, at least to me. A week later, one of our clients brought up a potential pivot with us, and our pro bono experience working with Shopify helped us advise them on what to do.

I wouldn’t change the decision, but I would try to do a better job communicating what we were doing and why to my team. Selling your team on a decision is more work than just demanding it happen, but the results are typically better.

Tips for your week:

Giving back can help you feel more in control of your situation. But be honest with yourself about the resources you have to give whether that’s money, time, or energy. And in an uncertain time, over-communicate, over-communicate, over-communicate. Sometimes it’s worth asking a lot of yourself or your team, but explain why you’re doing it.

Check in with your team and clients; be transparent

The first two weeks after we officially started quarantining, my schedule was non-stop meetings. I’ve been trying to cut back on the time I spend in meetings, but I don’t regret a single one I had during those weeks.

I checked in with all of our clients. I helped brainstorm new strategies where necessary or just made myself available to chat if need be. I spent just as much time meeting with our team, first over Slack and then in one-on-one video calls. We added a second partner meeting on top of multiple impromptu discussions about company strategy.

At first I wasn’t sure how transparent I should be in these meetings. I didn’t want someone, client or team member, to take something the wrong way. We had 3 months of runway in the bank. I figured if we didn’t sell anything else, we wouldn’t run out of cash until November. But would that figure comfort our team...or freak them out? Did clients care how our business was doing during all of this?

The more I shared, the better the conversations went.

Once I shared our runway with the team, they felt safer. By sharing the struggles we were facing with our clients, they were happy to find compromises that helped us both.

Tips for your week:

When the world feels like it’s crashing down around you, the best business move is just to be human. Reach out and talk to your team, your customers, and your friends. Check in on everyone and be as transparent as possible. Especially in uncertain times, transparency is what people need and respect.

Shore up your finances

In between meeting with clients and the team, my main focus became taking care of our finances. For several months I had been wondering if we should cut back our spending on software subscriptions. It never seemed worth it, but within half an hour I was able to save us close to $1000 per month. That was enough to nudge our project runway forward one month.

From there, I was torn on whether to focus on sales or apply for the government assistance programs. Then I realized a sale might bring in $75,000 if we’re lucky. That’s after weeks of follow ups and discussions. A government loan, on the other hand, could bring in ~$90,000 with a week’s worth of work. That made it a lot easier to decide where to focus.

Tips for your week:

Once the people in your business are taken care of, focus on finances. A time of crisis can make it easier to prioritize. Suddenly, those subscriptions you needed before don’t seem quite as important. And the little costs can add up. Beyond cost cutting, make sure that you take advantage of any government assistance available. Better to have it and not need it, than vice versa.

Adjust your marketing plan

We debated how much to change our content marketing plan. The work we’re doing right now falls into three buckets:

  • Newsletter
  • Blog posts
  • Sales pages

It was obvious the newsletter strategy should change. Because it takes less time and effort to write, it’s easy to justify changing up our content calendar for the newsletter. But at first, we thought we should stay the course with the blog and sales pages. That was, until we read this post from Rand Fishkin.

Ultimately, we decided to stick to our plan for the sales pages, but adjust the newsletter and blog posts we had planned for the next 3 months.

Tips for your week:

Things are never black and white. You don’t have to blow up your entire content strategy during a crisis, but you also don’t want to be oblivious to the situation around you. Find a balance between long term investments and short term changes that works for you. When in doubt, optimize for the short term right now.

Two steps forward, one step back

Monday I had a day where I was completely unproductive again. I got a few sentences written towards a blog post, and I set up a meeting with a sales lead. But for most of the day, I couldn’t focus.

I felt awful. I thought, “There’s clearly no time for days like that anymore, if I care about our business I’ve got to be more disciplined.”

I do need to be more disciplined, but I’m also choosing to be forgiving. This is all still affecting us in ways we don’t always notice. It’s important to extend that forgiveness to my team as well, while gently pushing us all forward. Kindness and forgiveness are far more effective tools than guilt and shame.

The next day I made sure to start my day with a run and meditation. I still got distracted and found myself falling into old patterns more than I wanted, but it was much better.

Tips for your week:

Remember this is still affecting us all. Be kind to yourself and to those around you. If you find yourself struggling, focus on the little things. Get back to the habits that make you happy and healthy.

What’s next?

Now that our team is more settled, our clients have updated their strategies, and we’ve double checked our finances, I’m trying to decide where to focus my time and energy next. The first priority is any inbound sales. I’m working with a handful of leads, mostly from before the crisis.

With my extra time I’m weighing whether to try outbound sales, something we’ve never been great at, or to work on new revenue streams.

The truth is, I don’t entirely know what’s next--no one does right now. But I know our team, our clients, and our community are in this together. I’m still putting one foot in front of the other, and I hope I’ve encouraged you to keep doing the same. 👟💜

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