3 Mistakes I’ve Made as a First-Time Venture-Backed Founder

Jul 08
Starting AlwaysHired has been the most rewarding experience of my life. It is the perfect combination of helping people and making money. Well, historically we have been more successful at helping people than making money, and that’s what this post is about. 

Being good as an individual contributor and starting a scalable business are two different things. 

Being good at sales leadership and starting a scalable business are two different things. 

Launching an app is different from building a scalable business. 

Hiring employees and signing customers are different than building a scalable business. 

Generating cash flow and creating a scalable business are two different things. 

I had all these assumptions that turned out to be wrong, or at least misguided. They say hindsight is 20/20, and it is best to learn from those that have tried, failed, tried again, and succeeded. They say that to truly move on, you must push through, not around. They say it doesn’t become real until you say it out loud. 

This post is the intersection of all those points. 

This post is to help me vent, to help our team and our customers understand that at AlwaysHired, we learn from our mistakes, and to support you and help you continue to create the competitive advantage that has made you successful in your career thus far.

Here are the top 3 mistakes I have made as a first-time venture-backed founder:

1 Team Building

The team is everything. Not the opportunity, not the product, not the vision. The team is the single most important factor in determining if execution on the opportunity, product, and vision will happen. 

I didn’t realize it was “Team” first, and then product, etc.

This shortsightedness was also reflected in my leadership style. I never thought people were the most important thing...how wrong of me. Smh.

2 Customer Retention

To be blunt, as a sales guy I was never incentivized to care about the lifecycle of the customer post-sale. After working in sales for 10 years, disregarding this caused me problems when I made the transition to company founder. 

In the world of technology, it is ALL ABOUT keeping your customers. Most people would argue, it is even more important than signing new customers. As Salesforce would say, we are now focused on creating “customers for life”.

This attitude, combined with my lack of practical experience in customer success and my lack of appreciation for having a good team (so at least someone else could fill this gap of mine), only compounded when we did not limit customer sign up upon launch. I was in the mindset of “more customers, more sales, more money” without realizing the implications of this. We were not ready for all of the leads that flooded in. I didn’t not understand the importance of individual customer interactions. And as a result, we had a lot of customer churn. 

3 Balance

Someone once told me that a person who works 100 hours/week will accomplish as much in 4 months as a person who works 40 hours/week will accomplish in a year. 

So guess what I did? 

Unfortunately, I did not have an exit strategy. All I did was work like crazy and at first it seemed effective. But soon after, I noticed that the quality of my work was diminishing, and I was feeling burnt out. I wasn’t the strong leader that I knew I could be. It was clear I needed an adjustment. 

Working 100 hours/week made it “easy” to go from Individual Contributor to Manager in a year, but as a Founder that meant it gave me one or two years of a head start, but then what? 

I was so busy running, keeping my head down, that when I finally arrived at my destination, I realized I was not where I thought I would be. 

I ran the entire length of the race, but I did not arrive at the finish line. 

So with shame, I had to turn around and retrace my steps, only to return to my last checkpoint...

...To start the last leg of the race again. 

But this time with a pace that is sustainable, and with a team that is hungry, capable, and feels appreciated.

So here we are, back on the right path. The path where our students have great experiences, our partners appreciate working with us, and I have time to write articles and focus on things like key growth metrics and employee career paths. 

If I could do it all over again, these are the 3 things I would prioritize: Team Building, Customer Retention, and Balance

Thanks for reading, and I wish you continued success on your journey! 


PS. Phew, I did it. I have had this on my mind for so long. It feels good to get it off my chest. We are our own worst critics, right?

PPS. To celebrate our new big push, we are waiving all contingency placement fees. This offer is only for our current customers, as well as the first 10 new customers to sign up on this plan. 

Email Shabana.fazal@alwayshired.com or schedule a call with her here: https://drift.me/shabanafazal.

About AlwaysHired Sales Bootcamp

AlwaysHired Sales Bootcamp is an intensive remote live instructor-led sales training program connecting hard-working and motivated job seekers with high growth technology companies across the country. Founded in 2015, it has 250+ alumni working at companies such as CallidusCloud, Google, Mulesoft, Okta, Yelp, Lever, Demandforce, and more.

For more information please visit https://www.alwayshired.com/. For media inquiries, please contact gatekeeper@alwayshired.com.
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  • Andre T. 2020-07-08 17:26:28

    Great post Gabe! Those three things combined with the passion and processes you already have in place will certainly amplify your presence and assist with scaling. Growth and great things are on the horizon, keep up the great work!

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