What I learned from my latest startup experience

Recently, I got a chance to start a business with an old friend of mine. We went for ten months before I realized that particularly business was not the right for me.

In those ten months, I learned quite a lot, and it gave me proof that I have the stomach to handle the intense startup roller coaster. There were definitely some dark days…

Here’s what I learned from my “failed startup experience:”

Sales is King

You may have a kickass product, but without a good sales person/org/machine, your company is going to die.

In previous roles, I often worked with sales people but I always held the position that Product was king, and I was making their life easier by making a great, useful and valuable product for them to sell. But now I realize that was true…to a point.

At my startup, I quickly realized without Sales, we do not have a company. Sales is what keeps the lights on and food in our bellies.

It came to the point that to keep our company going, I had to jump into a sales role myself, which was a real eye opener and you can read more about my B2B sales experience here.



Small Business is a tough market

As a company, we saw a great, overlooked business opportunity in the small business market. Here were thousands and thousands of companies within a 40km radius that were being overlooked, and we were going to swoop in, change their businesses…and their lives forever.

And the reason it was being overlooked were other players found the individual opportunities in the market to small and not worth it….the crumbs of the cake. Since there were so many crumbs and we were a leaner machine than our competitors, we could use the crumbs to make our own cake!

From my partner’s domain knowledge of the industry, he identified our sweet spot as small businesses who had between 5-35 employees, as most of these businesses would not have a dedicated IT/tech person, and we could easily swoop in.

But then as we started working in this segment of the market, we quickly realized a number of things:

  1. These business owners were strapped on cash flow, sometimes struggling to make payroll from time to time
  2. Since our ideal customers didn’t know much about technology in a business context, which is why they needed us as their tech advisors/partners, they were often laggards when it came to business technology

Since we had more of a concierge type of service, rather than a SaaS type model, #2 often made it difficult to close sales as we quickly found out that some of our prospects had lived with pains for years (often 5+) and were most likely to continue that trend. This reason was why they would always be a small business.

Product Strategy and Company Strategy are very similar

When it comes to starting companies, I’m no Richard Branson. But, I’ve created/developed a number of products during my four years as a Product Manager.

When we set out to start this company, we initially were a bit stuck, but thankfully I realized that starting a company is the same thing as creating a product. You need to identify why you are creating this product (aka your internal motivation), who is your target market, what are their pains and needs, and what you’ll solve and why you are the best one to solve the problem.

With this in mind, we thought our company as a product as we quickly realized when we were in sales meetings is that we needed to not only sell the product we developed, but also the company we developed. Trust was a major facet in every conversation we had.

Bootstrapping is hard

Starting and running a company without a single dollar from outside sources is hard. Thankfully I had some savings that I could dip into and there were some things I could do to minimize my costs, such as moving back in with my parents to avoid paying rent, working out of a home office so we could save on office rent and cook up own meals, and even reducing my social life.

Even with such “drastic measures,” there were still days where I didn’t even know how I was going to be able to buy gas so I could go see a potential client or even buy that client a coffee! During such times, we often had to put the dream on hold to take on non-related projects to keep the dream alive and gas in our cars.

Things got especially hard when it was time for us to scale our sales operation: 99% of the sales candidates wanted a base before their first sale! How could we offer them a base when we ourselves didn’t have some sort of salary to depend on!

I’ve always held the position that outside investment is a bad thing since it’s very easy for you to lose control of your company, especially when you are small, have no to few sales/customers and thus have no leverage. But after such an experience, I know understand how hard it is to operate without a consistent cash flow or investment, especially when you want to grow your sales organization.


Hiring is the toughest job of a Founder

When it was time for us to scale up our sales operation, I knew I had to invest a lot of my time on recruiting. I spent anywhere between 25% – 50% of my week talking to potential candidates, looking for that diamond who had the drive/ambition, knew how to sell, and was okay working initially on a commission-only basis.

Recruiting ended up taking so much of time as it was insanely difficult to find somebody who met the above criteria, especially since most wanted a base without actually producing any value for the company! But, if it was pivotal to the success of our company, so I rolled up my sleeves and bit the bullet. I ended up interviewing over 50 candidates before I eventually hired 2 of them who fit the profile we wanted.



At the end of the day, I feel incredibly grateful to be able to have gone on such an experience. I’ve learned and grown so much over the past ten months than I think I have in the previous four years! Not only has this experience made a better Product Manager and will help be more successful in my next enterprise, but I feel it’s made me a better person. Booya!

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