Episode 16: Businesses Jacob Started That Failed, and What You Can Learn From Them


I have been an entrepreneur for a long time and over the years I have started several businesses, some have worked well and others have not. Today I am going to share three businesses I started that failed and the lessons I learned along the way. Hopefully you can learn from my mistakes and apply these lessons to your own journey as an entrepreneur. 

Failure is a state of mind

In my early 20s when I still had a full time job inside of an organization I started a company based on affiliate marketing and SEO. I had become disengaged at my regular job and I wanted something on the side that I could enjoy and make money from. Basically I had a website that acted as a hub for larger sites like Amazon to sell through. I eventually quit my full time job and I spent all of my time learning about SEO and how to get websites ranked. I worked on this business for over a year and I wasn’t making any money at affiliate marketing. Ultimately it failed and I had to let it go. 

But I learned a lot from this experience. First of all I learned failure is a state of mind. Failures are something to learn from and they can be applied to things you do in the future. Being able to take those lessons into future endeavors is very valuable. This failure in my life played a huge role in where I am now. It was because I spent so much time learning about SEO that I was able to get a job in the Bay Area, where I still am today. 

Another lesson I learned from this business is the importance of learning how to learn. I leveraged a lot of free tools I had at my disposal to educate myself in SEO and other valuable things. I found out that I could easily learn things on my own without a lot of money. 

Pay attention to the signs

The second business I started was one I was in with a couple of friends. We created a company which provided a social network for neighbors, it was basically what Nextdoor is today. We tried to deploy this platform in different condos and complexes in our area, but it never really took off. And we eventually gave up on it. 

What I learned from this failure was that I was not in this venture for the right reasons. I wasn’t passionate or excited about the company or what we were doing. Basically I was just in it for the money I thought we would get and for the job title, Chief Marketing Officer. 

I also realized later on that there were signs all around that it wasn’t going to work. We weren’t able to raise money, people who used it didn’t like it, one of our business partners walked away. I should have seen it coming, but I tried to ignore the signs. 

The People You Surround Yourself With Matters

Another business failure I had came later on when I started a consulting company with a group of four or five others. We were consulting companies around customer experience stuff and also workplace tools such as Chatter, Yammer, and Jive. We were working with them to figure out how they could utilize these tools and technologies to connect with their employees and also with their customers. 

Ultimately this one failed because our team did not have great dynamics--it was not diverse or inclusive. We all had the same strengths and the same failures so we didn’t compliment each other well. We didn’t have anyone bringing in different ideas or thoughts. We also didn’t have a clear purpose or a clear path forward. 

The main lesson I learned from this experience was it is important to have the right team around you. The people you surround yourself with should not be exactly like you, they should bring different thoughts, ideas, and experiences. And you should all have different strengths and weaknesses to complement each other. 

So there are several lessons I have learned that I have brought with me in all of my other business ventures even to this day. So here are some challenges I would like to present to you that you can use to learn from my failures. 


  1. Think about your recent failures. What have you learned from them? How can you apply those lessons to your current role or future opportunities? 
  2. Why do you want to start a business? Are you in it for the right reasons? Are you just chasing money or a job title or are you genuinely excited about the prospects? Don’t forget to look at the signs around you. Do you see any signs that warn you to get out or try something different? 
  3. Do a quick audit of who you surround yourself with and make sure you have a diverse and inclusive team. Do you know your strengths and weaknesses? Do the people on your team compliment your strengths and weaknesses? 

Don’t beat yourself up if you have failures. We all need to have failures. The main point is that failure is a frame of mind. Don’t view failures as things that you can’t overcome, view them as things you should overcome. Failure is a part of life, a part of business, and definitely a part of being an entrepreneur. 

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