For Starters: The Reality About Being Your Own Boss

On the third episode of For Starters (now available on Apple podcasts!), host Robbie Allen picks the brains of local entrepreneurs Adam Smith and Kelly Pfrommer about what they have learned from their experience being their own boss. Before founding the SaaS startup Wrangle last year, Smith previously worked at CED, , Square 1 Bank and StatSheet—which became Automated Inisghts, and is where he met Allen (who was the Founder and CEO).

After getting the Salesforce bug while working at RedHat, Pfrommer started her own Salesforce consulting company Cloud Giants in 2014, where she is currently CEO, as well as at Salesforce-based software startup RevdUp. 

Pfrommer and Smith discuss the benefits and drawbacks of being the No. 1 in the office, with both mentioning that while leading a team and getting the final say on decisions comes with an incredible amount of burden and responsibility, the rewarding feeling of pride in their team and employees well makes up for it.

Here are some of the highlights from the episode:

  • Spoiler alert: you still have to listen to other people even when you start your own company. As Smith put it, “If you have customers, investors, or employees—you have bosses.” In other words, yes, your customers can fire you. So while the buck and totem of control does stop with the boss, Smith warns against playing dictator and steamrolling other ideas. (17:50) 
  • Smith said the coolest thing about being the boss isn’t the fact that he controls his own schedule or is building something new (but those are pretty boss), but the honor he feels in leading a team and the rewarding feeling of seeing employees’ families and kids at holiday gatherings. (20:40)
  • Pfrommer talks about the interesting evolution of being boss, as she went from being the sole expert about Salesforce and training new employees on it to learning from her employees as they became the experts. (31:10) 
  • Being curious and having a willingness to learn is key when starting a company. No one is ever 100% prepared or qualified to dive into the waters of entrepreneurship for the first time, but the great thing is that you will learn as you go, which is why Pfrommer says she stays as open-minded as possible. (44:00)

To listen to the full episode, click here: