096: Go out on the skinny branches with Jeremy Cherny

About Jeremy Cherny 

Jeremy Cherny is a techno-nerd and entrepreneur. He loves business, educating people on the possibilities of computers, building teams, and creating leaders. So obviously he started an IT services company! As President and CEO of Tobin Solutions, Jeremy drives its mission of providing a better technology experience to business customers giving them better IT service, better IT strategies, and solutions for better business outcomes. Tobin Solutions was named Milwaukee's Best Places to Work!


I heard you won an award for Milwaukee’s best places to work! How did you do that? (1:30)

“I got some advice once about running a business. And they said that my number one job as a business owner and leader is to build a team. And so, I looked for, how can I actually measure that? And had the idea that… if you are one of the best places to work, you have to have a pretty great team.”


Should I be concerned about social media security? (3:00)

“Yea concerned not like losing a lot of sleep over it, but pay some attention to it…”


What are the keys to success in business? (6:30)

“Be coachable. I don’t have all the answers, and just listen to other people. Use the experts, don’t reinvent the wheel on things. And persist through the failures…”


Share with us one of your best networking stories (8:15)

“one of the vendors we use for helping us find new team members, a recruiting firm had a networking event, networking customer appreciation event. And you know sometimes I go, sometimes I don’t and for whatever reason I chose to go to that one… and I ran into somebody, a guy that ran a much larger IT company…”


How do you stay in front of your network or community? (11:00)

“We do the traditional things, so we do a newsletter, we send that out monthly… and then we use Facebook, and Twitter, and LinkedIn, and then I use Buffer tied to just whatever I’m reading…”


What advice do you have for business professionals looking to grow their networks? (14:00)

“There’s a lot of tried and true strategies out there. So, kind of in that vein of being coachable, and not reinventing the wheel, just pick one of those strategies that are out there.”


Digital networking or traditional networking? (15:45)

“traditional ultimately. And I think its just part of that conversation, there’s such a high trust factor when you turn over IT to somebody.”


If you could go back 20 years, what would you tell yourself to do more or less of regarding your career? (17:15)

“be coachable. Don’t take life so seriously, you know have some fun with things. And really stop trying to do it all on your own. Engage people, build a team”


We’ve all heard of the 6 degrees of separation… Now, who would be the one person you’d love to connect with and do you think you could do it within the 6th degree? How would you start that journey? (18:15)

“one of the shows I really like is “comedians in cars getting coffee” with Seinfeld. I would love to be on that show. I don’t know how funny I am. But just to have a conversation with him would be terrific, and how I would do that I don’t know. I would probably start with social media…”


What book are you reading right now? (22:00)

“I just started, its called “the speed of trust” by Stephen Covey…”


Any final words of advice for our listeners? (23:47)

“just keep at it, just don’t give up, never give up. That’s really it. Its pretty straight-forward. And if your stuck go seek the advice of professionals so you can get some new ideas and new actions to take.”



You can get in contact with Jeremy at:

Find him on LinkedIn


Email him at Jeremy.cherny@tobinsolutions.com