Hey Sasha: It’s 5… time to move on.

James Orsini
3 min readDec 29, 2023

By James Orsini

It’s hard to believe we started The Sasha Group more than 5 years ago. As you all know by now, the number 5 has significant meaning for Gary Vaynerchuk. It was at 5 years old that he requested a Jet’s Football Jersey from his mom. As the story goes, the poor Russian immigrant family did not have disposable income for a football jersey, so Gary’s mom knitted him a Jet’s sweater with the number 5 on it. To this day in virtually every photo op, Gary can be seen holding up 5 fingers as a reminder and tribute. Note to self, don’t grab his hand. https://youtu.be/XGMEVBfGSeo?si=WppiFd8tqiE8IX7L

Today I reflect on my 5 years at Sasha. I believe it is one of the longest tenures I have stayed in any single position in a nearly 40-year business career. I just re-read the various Medium articles I have written over my years at The Sasha Group. From a little under $10m in revenue in Year 1 and around 30+ people to now $20.5m in revenue and more than 110 employees. The first year 2019 had the article “The Sasha Group a year in review a decade ahead”. It’s the first time we used the term Start Right to describe what we launched rather than start up. We pulled together Fortune 500 experience with Entrepreneurial DNA in 7 leaders to launch 3 pillars around Education, Consulting and Marketing for small and medium sizes businesses.

Year 2 saw the article “Sasha 2020- A dream without a plan is nothing more than a wish” where we introduced the Eisenhower Matrix. A decision tree approach we still use to this day. We grew to $12.5m and had around 60 employees. Year 3 “Sasha 2021… Tag You’re it!” introduced the concept of tag lines. Our north star was Sasha the Heart of VaynerX. Our foundation was Consultancy meets Agency, Strategy meets Execution and Smart meets Heart. We grew to $15.5m in revenue and 75 people.

Year 4 2022 took me back to the article “From Saatchi to Sasha” where we reminded ourselves to be fearless in an industry of fear. We remind ourselves there is nothing we can’t do. We saw revenue climb to $17.5m and staff nearly 100. And now in year 5, where we lean into productized offerings, we see the return of some clients who were in our hallways, exit, and have now come back. Revenue is now $20.5m and more than 110 employees.

In 2024 I take on a new role as President of Start Up Operations for VaynerX. After 9 years in the VX family this will be my 4th title and 5th role I’ve played for Gary. I wish to welcome my friend and colleague Marcus Krzastek as the new President of The Sasha Group. I am certain he will take Sasha to the next level. I wish to thank each of the leaders (past and present) for all their efforts in our success to date. Kyle Arango, Jason Chan, Mickey Cloud, Nick Diodato, Mark Evans, Katie Hankinson, Jesse Hutchison, Maribel Lara, Jason Loomis, Jared Nixon, and Joe Quattrone upon your backs I stand. Special thanks to Gary and AJ for always believing I could provide some benefit in their hallways. I look forward to the new challenges ahead at VaynerX.

--

--