4 Lessons I Learned The Hard Way As A First-Time Founder| ItSoftNews

When you’re starting a business, you’re signing up to dedicate a good part of your life to it. Starting and scaling a tech business is hard–brutal, even–especially right now with the tech correction, inflation, hiring, and supply chain issues, but you don’t truly know how much of a roller-coaster it can be until you do it. 

The truth is nothing can fully prepare you for becoming a founder. Some lessons need to be learned through experience, and there will be lots of problems you never see coming (for example a global pandemic). But there’s some basic advice that I think applies to every entrepreneur. Here are four things I wish I’d known before starting my journey more than a decade ago. (Disclaimer: I’m not the first person to give this advice and you’ve probably been told at least some of this before, but that’s because it works, and it’s important enough to listen to again.)

Have a cofounder 

You might disagree with me on this, and you might be right. Having a cofounder isn’t for everyone, but it was absolutely the best move for me to found Jobber, an operations management platform, with Forrest Zeisler, our CTO. The cofounder relationship is unique, and having someone by my side on this journey has been invaluable. As a founder, you need to wear a lot of hats, and it helps to be able to divide all the work that needs to be done with a partner, especially if you have complementary skill sets or enjoy different kinds of essential work.

You can have vulnerable conversations with a cofounder that you can’t with anyone else. Forrest and I have had many open and honest conversations about our doubts and fears relating to the business, being responsible for the livelihoods of employees, and balancing life outside of work. You can share burdens and challenges with a cofounder in a way that is difficult or impossible with just about anyone else, and that’s valuable.

Don’t give in to the pressure to pivot too quickly

The startup world is plagued with “pivot culture.” The moment things get too hard, or don’t go the way you thought they would, there’s pressure to find a new direction. At Jobber, we were early to our space developing SaaS for small- and medium-sized businesses–and we’re actually working with very small businesses, most between 1 and 30 people. So, we had a hard time raising money early on; a lot of investors thought our customer segment wasn’t compelling enough. We had to push hard for years before it was clear that our idea was going to be successful and we could scale. 

We kept pushing because, even though things didn’t go the way we thought they would, we had validation from our market. It’s important to always be talking to your users, and to build up your own conviction about what you’re doing. Jobber began because of stories we heard from small business owners struggling with paperwork, organization, and all the administration work of running a business. I continued to spend hundreds of hours connecting with customers over coffees and lunch early on, and the experience sparked new ideas that we wouldn’t have uncovered otherwise, and had a profound impact on how we built (and continue to build) our product and our business.

If you believe in your idea and you’ve validated it through research and conversations with end users, don’t be too quick to abandon it.

Hire people who truly believe in your mission

Take the time to figure out why you’re doing what you’re doing and what impact you want to make, then find the people who want to help you. 

It’s not just about hiring the smartest people or the ones you’d want to be friends with. Especially early on, the people you hire will shape your company culture and values, so look for constructive and collaborative people who are eager to contribute to what you’re building. These are the people who will have the biggest impact on the cultural direction that is established from the outset, so they should connect with your mission and how you’re trying to make a difference in the lives of your customers. 

This is especially important when you begin to grow your leadership team. These are the people you’ll work most closely with, and will have outsized influence as the company grows, so spend time building trust. Your working relationship should allow you to be direct–there are plenty of difficult, constructive conversations in your future, and you want to discuss solutions quickly and candidly. Test out your working dynamic with leadership candidates by solving a small problem together as a way to test compatibility. If you can solve these problems amicably and efficiently, that’s a good sign for building a long-term business relationship.   

During the early days of hiring at Jobber, we had an instinct to hire people who were really engaged with our customers–some of them entrepreneurs themselves–and were excited about making their lives easier and better. We weren’t consciously looking for these qualities when we started, but ultimately it helped us establish a strong foundational purpose, culture, and values to build on. When we sat down to actually formalize and define them, they weren’t aspirational–we were already living them.

Consider your early-stage investors thoughtfully

Early investors can have outsized impact on your business, so beyond the capital they contribute, you should make sure they align with your vision and can provide useful advice and an outside perspective. 

Early stage investors are signing up for a journey with you, and there will be rough patches along the way, so you want them to believe in your vision and plans for achieving success. The last thing you want is pressure to pivot when you hit your first bump in the road. 

The insights, partnership, and connections our early investors provided were so beneficial and valuable to scaling Jobber. We were fortunate to raise capital from two early stage investors who were very involved as educators, coaches, and mentors. They were critical to our early and ongoing success.

When we first started Jobber, my cofounder and I were meeting to work in a coffee shop. Now we have two offices, over 500 employees, and 160,000 service professionals using our software. I’m not sure I could’ve imagined this when we started. There have been many challenges, but we’ve also had the opportunity to build a business that I’m passionate about, give others career opportunities, and help our customers be more successful in their own businesses. 

It’s important to remember that you can’t avoid every pitfall that comes your way, and setbacks and mistakes are part of the journey as a founder. It’s important to see them as learning opportunities, and become better because of them. This has been a tough journey, but also one of the most rewarding. I hope my experiences help you as you get started building your own business. Good luck!

Sam Pillar is the CEO and cofounder of Jobber, an operations management platform for small business.


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