Home » Latest News » Entrepreneurs » 5 Mistakes I’ve Made While Creating My Startup: Jon Staff

5 Mistakes I’ve Made While Creating My Startup: Jon Staff

Top 5 Mistakes I've Made While Creating My Startup

At Getaway, we manage to get some things right. Customers consistently give us high marks in the 80s on our Net Promoter Score (NPS), and our employees consistently give us high marks in the 70s. We’ve managed to keep those figures stable even as we’ve expanded our globally dispersed, asset- and people-heavy business at a breakneck pace.

We recently reached one million followers on Instagram. I’d be happy to boast more, but since we all know that failures teach us more than triumphs, I’ll instead share some of the blunders I’ve made (so far). I’m hoping that you’ll be able to apply some of the generalizability I’ve found in my industry to your own.

Battle Approved Motors. Invest Today!!
Get a $250 Amazon Gift Card. Apply Today!

HR was established too late, and it took too long to perfect it

I put off establishing HR (or people and culture, as we call it) for a long time, and when I finally did, I made several unsuccessful attempts before getting it right. No one was nagging me to prioritize human resources, but now I see that was a huge mistake.

We run a low-barrier business that depends on a large number of people doing their jobs well on a daily basis. The entire HR toolkit, including talent acquisition, training, and employee retention, must be in place to make such results routine.

Reluctant to bring in seasoned executives

Some of the lessons we are taught in startup land are always true, while others are simply incorrect. Most people are correct at first, but they eventually become incorrect. Leaders of startups teach their followers to save money wherever they can, and we are taught to distrust seasoned leaders in favor of ragtag groups of believers (usually in a garage).

At first, I thought both lessons were spot on, but they started to diverge after a while. Looking back, I realize that after we got our first major funding round (Series A), I should have moved faster to put together a C-suite leadership team with relevant experience.

That’s what I think would’ve helped us expand more quickly and steadily. Don’t take my words out of context; I just think it’s smart to be frugal in general, and I wouldn’t hire someone with a blue-chip corporate “name” if they haven’t worked in a growth company before.

Underinvested in our real estate pipeline

We have accomplished a great deal of expansion by means of “rabbits out of hats,” which is not a strategy and introduces a great deal of uncertainty that is detrimental to the team.

We could have avoided a lot of this trouble if I had stopped trying to piece together a solution in time to win the month, quarter, or year and instead worked on making a system and funnel to turn real estate leads into working Getaway Outposts.

We abandoned our regional center

We had a headquarters team in downtown Brooklyn before we had to evacuate because of the pandemic. The cultural costs and the number of adjustments needed to make this work well have been higher than I had anticipated, despite the fact that it has had many positive effects.

I am not suggesting that we all return to the 9-to-5, but if I could change anything, it would be to make it within a day’s drive of New York City a requirement for working at or joining our headquarters. This would have allowed us to hold more frequent team meetings.

The basis of a brand

In all honesty, I couldn’t be happier about all the praise that has been showered on our name over the years. Still, I would have spent much more time, in the beginning, having deep, philosophical discussions about our long-term goals and then mapping those objectives onto a brand architecture, an intellectual property strategy, a graphic system, and supporting products like merchandise.

In contrast to changing as you grow, slowing down at the outset saves a lot of time.

I’m sure there are other errors on my part that aren’t included here. I’ll tell you the rest of the war stories over a beer one day, but for now, I hope these will help you and our team avoid the wounds I’ve suffered.


About Editorial Staff

The Editorial Staff is a dedicated team of writers and editors who oversee the content of a leading news site. With a commitment to accuracy, quality, and unbiased reporting, they work tirelessly to deliver up-to-date news articles that inform and engage readers. From researching and writing compelling stories to meticulously editing and fact-checking, the Editorial Staff ensures the highest standards of journalism are upheld, providing readers with reliable and trustworthy information in an ever-changing news landscape.