Partner Spotlight: Becoming an Entrepreneur with The Dalessandro Group

JCU Alumni Dinner with Gina Dalessandro

JCU Alumni Dinner with Gina Dalessandro

“I think we’ve actually met before,” I said to my then-mentor at a John Carroll networking event, referencing the woman he introduced me to: Gina Dalessandro of The Dalessandro Group. She nodded in agreement. When we reviewed our backgrounds, Gina and I had actually met multiple times before—as contractors for the same company (working on different projects) and at networking events around town. I would end up meeting her daughter, Alysse, a couple years after that event by chance when I wore a “Cleveland” shirt at a retreat both of us attended.

Gina Dalessandro not only runs The Dalessandro Group, but she also volunteers for organizations like the John Carroll National Alumni Board, runs CREW (a women’s networking group), and is an incredibly talented Cleveland connector. 

Beginning The Dalessandro Group

I don’t think I ever asked you how you started The Dalessandro Group, which seems funny to me since we’ve known each other for many years now.

I really have a multitude of things in my background. Even though I started out as an accounting major at John Carroll, I quickly found out that even though I love numbers, accounting wasn’t for me. I then decided to go into marketing because I was more of a people person. The real eye opener was: When you get out of school, you think you’re going to go right into marketing. Most of the time, companies want you to go in through another route like sales. So I started out in sales and was very successful.

I started my first consulting business after I had my first child, and I was able to do it part time a few days a week. 

At one point, I worked for a midsize company. I was VP of sales and marketing, and I got a lot of good experience there. The owner was very open-minded, so I got to try all different kinds of marketing techniques.

I worked full-time for the American Diabetes Association for a while. (My marketing background definitely helped me out there.) And then I decided when the girls were approaching college that I needed to go back into the for-profit sector, so I did.

From there, I met someone who turned out to be my business partner, which was my last entrepreneurial stint before my current company. That went well. We developed our company from $0 to $1.5 million in less than five years. I was the salesperson, and it was fun. I did a lot of it through former client relationships. We had a work loft space in AsiaTown and invited each of those companies to have lunch with us hoping they would come over to our new company. For me, it’s all about building relationships. Many of them started to do business with us, so we got a good running start. 

When I decided I wanted to go off on my own, I had thought about it for a year. I was trying to figure out where I thrived with my talents, where I saw a need, and how I could give back. I ended up being on five different nonprofit boards at the time.

With those experiences and my background at the American Diabetes Association, I saw that nonprofits were always underserved, underfunded, and usually understaffed. My whole premise at the start of The Dalessandro Group was to help them. I also had some of my former for-profit sector clients come back and ask to work with me again, so I ended up with a nice blend of nonprofits and small to midsize businesses. I’m trying to think how many years it’s been now.

Struggles and Bright Spots of Entrepreneurship

Gina Dalessandro of The Dalessandro GroupI’m sure after a while, it all blends together, especially since you’ve had those entrepreneurial stints throughout your career. It’s wild to think about those milestones years-wise. And the process to get there is hard. Sometimes, people romanticize entrepreneurship, but it’s not for everybody. There are definitely days when it’s great and days when you don’t know why you’re off on your own.

Yeah, they don’t see the behind-the-scenes when you’re working until 11:30 p.m. or you have an event and are filling in on weekends. Or it’s a cold morning but you have so much to do, so you crawl back in bed at 5:30 a.m. with your laptop to work on a project.

Also, when you’re a solo entrepreneur, you don’t get to go on vacation and have someone take over your work. It’s like having a child. It’s always on your mind. I think that’s what people don’t realize.

Would you say that’s the most difficult part—not being able to let go of your business when you go on vacation because you’re a solopreneur?

I found a way to work around it for the most part. I never have my “away” message on; I’m always in tune. A couple summers ago, we were in Hilton Head for two weeks and I didn’t let any of my clients know. I still took zoom calls and had shorter work days.

I think the most difficult thing for me is trying to find a way to balance the business—the number of accounts I want to work with and the size of those accounts. That also goes for projects too.

In this particular business, unlike the last one, I don’t have my own employees, just 1099s. I’m always keeping in touch with them and am looking for new people to get involved with because if I do get a new project, I might have to bring in somebody to help. And I also have to make sure there’s enough money in the project that I can pay them.

Especially as women, it’s important in my mind and I know it is in yours too, to pay people fairly, since we typically make less than men. Sure I can afford to pay someone $10/hour, that’s not fair for someone who has five years of experience. It’s tricky to find that balance.

Kind of a tangential question, do you have any stories of challenging moments, triumph, or anything funny that comes to mind?

For me, the challenge has always been constantly rebuilding. Just like any sales job, you’ll have your funnel full and be so busy that you don’t have time to meet new potential clients, so you’re focusing on working with those customers. Then you see it slowing down and have to rebuild again.

I had a couple surgeries that made me miss some of my clients’ events, and it was disheartening that I couldn’t go. I sent my two interns who took pictures and texted me all night. The customer was happy. I also relied on my daughters; they answered all my emails for me when I was tied up in the hospital. That was a real eye-opener for me. You just don’t think about what happens if you have to stop working for a while as a solo entrepreneur. You have to think about it ahead of time.

The Importance of “Thank You”

Definitely, and I think COVID really showcased—as a direct example for everyone—the importance of making alternative plans.

As a solopreneur who outsources work as well when the project necessitates, I had to get help when I went to Alaska. You have to explain so much before you go, even if you’re contracting out or if it’s family that’s helping you. 

Gina Dalessandro in Front of Italia Door

Through COVID and even beforehand, entrepreneurs have had so much tenacity because of all these extra considerations. What are some of the other qualities you think effective entrepreneurs might have?

Consistency and follow-through. Problem solving is also helpful. If I can’t do exactly what my client needs, I’m going to try to find another solution and deliver on my promises. That’s why relationships are so important. All my customers ended up being friends. I still have people who were on my committees at the American Diabetes Association 20-something years ago who I’m still friends with. When I was working with United Cerebral Palsy, I contacted quite a few of them, and they helped me on that project, so that was wonderful.

Another quality is being humble. I always appreciate my customers and thank them. The same goes for anyone who volunteers or works for me. That personal touch of saying “thank you” with a “thank you” note really helps.

“Thank you” notes are such a lost art. You especially are so good about that. I’ve always loved writing to people, but I’m nowhere near your level of “thank you” note writing, so I bow down to you, the master “thank you” note writer.

That’s so funny. You know, during COVID when things took such a turn, I had checked into starting a business around writing notes.

Yeah, I remember that!

It didn’t end up working out, but fortunately, because of that extra time, I found a way to do business with people in Europe. I ended up starting with one wine company, The Italian Wine Selection, then ended up working with three different ones. They couldn’t come here, so I was their feet on the street when we were allowed to go out, but I also helped them with their marketing and researching how they could do business in the U.S.: making those contacts, cold calling, setting up zoom meetings. That really got me through COVID.

The Dalessandro Group and Career Highlights

Definitely important to pivot. I think some of the best points in a person’s career are when they pivot and gain clarity. What’s another career highlight that sticks out to you?

I was working with a smaller nonprofit that ended up being absorbed into a large healthcare system. Those two women introduced me to Trish Otter (who was the CEO of United Cerebral Palsy at the time). It was at a networking event at someone’s house, and they said to Trish, “You really need to work with Gina. She’ll be able to help you, and we love working with her.”

I followed up with Trish and went out to lunch a few months later. We talked about what her issues were, and afterwards, I sent her a letter with six different ways I thought I could be of service to her. That was July or August, and some time that Fall, she asked me if I could come down to meet with her employees. After she saw they liked me, she told me their board wanted them to do a gala. It had been 20 years since they’d done one. She asked me if I’d be willing to help. In the end, we had way over the expected number of attendees. I think 350 people came, and we were well over our projected dollars raised. It was a nice way to kick off the first year of The Dalessandro Group.

It’s always great to see those things come together when you’ve worked so hard, not only for that specific event, but you’ve worked so hard in your career to build up your experience and your network to make events and projects successful.

It’s interesting because, when I look back at my career, I think about how many different things I was involved with: large corporations, smaller corporations, my own businesses.

I always wanted to be a personal shopper at Nordstrom, so at one point, I did that. The woman who was going to be in charge of the store opening up near me was in California, so I got connected to her virtually. She said she already filled all the positions but wanted to meet me. We set a date, and she came into town. The store wasn’t even done at the time; you had to wear a hard hat to go inside. I sat in the back of the room with her, and she happened to say during the conversation, “Ya know, I could really go for a muffin and a cup of coffee.” We had a nice conversation, and I left. Then I got her a cup of coffee and two muffins and delivered them.

On the same day we were moving into our second home, I got a call from her, and she said, “I’m ready for you.” But I wasn’t ready. So I started very part time, but when my primary employer sold the business, I did that for a while. I was glad I did that too because I formed a lot of friendships and did a lot of presentations at country clubs.

When I started at the American Diabetes Association and needed volunteers, I went back to those socialites, and they helped build up the events I was working on. One thing always leads to another.

Yeah, and not discounting any type of experience that you have. I edited a book by my friend, Josh, called “I’m Not a Copywriter, But…” which talks about that concept too. He had all these different life experiences that led him to become a copywriter. Similarly, you and I have our life experiences that make up who we are as marketers and salespeople. It’s great to hear you used all those connections to help with other positions you had, and those other transferable skills still apply to the Dalessandro Group as well.

Can you think of a time someone was particularly encouraging of you, knowing that all your experiences have led you to your unique brand of marketing?

Gina Dalessandro of The Dalessandro Group

I met two guys through COSE (Council of Small Enterprises)—totally different businesspeople, one closer to my age and one young guy—who really encouraged me. One is a CPA, so he talked to me about how I could make sure money was coming in. The other gave me free office space for my first year in business. I was always appreciative of them and kept in touch.

After I went through my one surgery, I thought, “I have to rebuild this business again.” So I called them and said, “Here’s where I’m at; what do you think?” They were both super encouraging still.

The one said to me over the phone, “I have something to tell you.” So I pulled over because I was driving. He said, “The most important thing you need to know is you are Gina. Who else is Gina? I don’t know anybody else like Gina who could do this. You need to know that there aren’t many Ginas around like you.” He was my cheerleader at the time. He said he had no doubt that within a couple months, I would have plenty of contracts again. It was so nice to hear, because who tells you positive things all the time when you’re an adult? It was also pretty accurate, since I went on to get four more contracts just months after that call.

Agreed! We hear those words of encouragement less and less as adults. It was so nice to sit back and hear your story. Obviously, you know I love stories. And we never really got a chance to talk about all of that before.

Me too. It makes you realize how much you miss when you go back down memory lane. I recently cleaned my office, and I had binders and binders of samples from fundraising and different projects. I ran across a notebook I had when I was brainstorming about what my business would be. That’s one thing I would tell a new entrepreneur, and I know Alysse has done this too: Set your goals, and have them some place visible. I’m a big believer in “If you write it down, it will happen,” and “If you say it, it will come true.”

This series seeks to get to know our collaborators (our awesome clients) and our partners (people we refer to help our collaborators with projects that aren’t our specialty)! You can read our previous interview with L.A. Carr by clicking here.