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Jackie Hermes of Accelity: “Entrepreneurship is not as sexy as you think it is”

Entrepreneurship is not as sexy as you think it is. Everything you see online is a highlight reel. I think entrepreneurs are getting more “real” about what it’s actually like to build a company but there is not a lot of information out there about how hard you’re going to have to work and the […]

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Entrepreneurship is not as sexy as you think it is. Everything you see online is a highlight reel. I think entrepreneurs are getting more “real” about what it’s actually like to build a company but there is not a lot of information out there about how hard you’re going to have to work and the incredible weight you carry as you build a company. I have lost enough sleep for a lifetime, worked many 12+ hour days, and I see no end in sight. If you’re going to get started, make sure you’re doing it for the right reasons.


As part of my series about the leadership lessons of accomplished business leaders, I had the pleasure of interviewing Jackie Hermes.

Jackie Hermes is the CEO of Accelity, a Milwaukee, Wisconsin-based agency that helps software-as-a-service (SaaS) startups get to revenue and grow faster, and a co-founder of Women’s Entrepreneurship Week. Very active on LinkedIn, Jackie sparks discussions about the daily life and challenges of growing a bootstrapped company. Jackie mentors student startups via The Commons, is a co-organizer of Startup Milwaukee EMERGE, an advisor with Golden Angels Investors, and mentors numerous early-stage startups. In addition to her professional involvement, Jackie is an adoptive foster parent and future pilot.


Thank you so much for joining us! Can you tell us a story about what brought you to this specific career path?

Absolutely. I graduated with a marketing degree and got my MBA without any real idea of what I wanted to do with it. There are tons of different kinds of marketing careers, and they can be hard to come by with the number of people competing for those jobs. I was lucky to have the chance to manage the marketing department at mid-sized software company Zywave at a young age (23)… I was basically trial by fire. The company was owned by Vista Private Equity and everything moved quickly. I loved the pace of software. At 26, I left the company to start my marketing agency Accelity. I saw a serious need for smart marketing at software as a service (SaaS) startups and was able to quickly build a nationwide client base.. We have a team of 15 marketers located in Milwaukee and are now back to growing quickly after some COVID struggles last year.

Can you tell us a story about the hard times that you faced when you first started your journey?

Gosh, most of the beginning was hard times. My company is bootstrapped — we have no outside investment, and I’ve never even taken out a loan, because I wanted to cash flow the whole endeavor with as little risk as possible (very midwestern of me). That led to a lot of financial struggles — I had to choose whether to pay my employees or myself more times than I can count. I thought about shutting down the company a number of times because it was so difficult, and money stress is about the worst kind of stress I’ve experienced.

Where did you get the drive to continue even though things were so hard?

I have failed a million times — of course, we all have, but I really hate to fail. There were so many people who said I would and doubted the risk I was taking and I had to prove them wrong… but mostly, I wanted to prove my own self-doubting wrong. It definitely helped that I had kids and at the time, a husband at home who was building his own business, and they were all counting on me. Quitting really wasn’t a choice. It felt really rough at the time, but looking back I am so grateful for the pressure. I doubt I would have kept going if there wasn’t so much at stake.

So, how are things going today? How did grit and resilience lead to your eventual success?

Today, my company is in a much better place, and so am I. We took a big hit when COVID started (we lost about 40% of our business), but we were able to buckle down and rebuild. I think a big part of us getting back on track — again — is that my mindset is so different. I put so much work into the way I think and the way I speak to myself on a daily basis that I know I can overcome any challenge now.

What do you think makes your company stand out? Can you share a story?

My company is comprised mostly of women professionals which is rare — our leadership team is 80% women. Most of our team members are also very entrepreneurial, having either run companies in the past, or currently working on side hustles and hobbies while they’re at Accelity. I think the fact that we are all so entrepreneurial, yet still dedicated to growing Accelity, is very different from most businesses. Most marketing agencies hate when members of their team have “side hustles” and we totally support our team. As it should be!

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

It’s easy to burn out when you work at an agency. There are a lot of clients to manage, and lots of competing priorities. I think the way you manage your own stress is the most important key to success…because when you have a handle on the way you act and react, you can stay calm in every situation. I talk to my team a lot about mental health, self-care, and managing our own wellness outside of work so we can bring our very best self to work.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

I am very grateful for my business coach, who I’ve been working with for nearly 6 years. She’s actually a good friend of my stepmom’s, and I really didn’t want to meet her at first. I thought there was no way I needed a coach! Ha! I’m glad I met her and started working with her because she’s helped me take my ideas and structure them. Accountability is key when you’re building something, and she makes sure I follow through on all of the things I say I’ll do. As a solo founder, I need accountability more than anything.

How have you used your success to bring goodness to the world?

I try to give to others as much as I possibly can. I do a lot of calls with new entrepreneurs to answers their questions about how to get started. I mentor women through Building Brave and student startup teams through The Commons in Milwaukee. I also put out a lot of content (mostly on LinkedIn) about what it’s like to build a business to let other professionals know they’re not alone and spark valuable conversations. Finally, I was a foster parent for two years, fostered a number of girls, and two of my three babies are adopted. I wish more people would consider fostering and adopting; it’s desperately needed all over the United States and you can change the lives of children and your own life in the process!

What are your “5 things I wish someone told me before I started leading my company” and why. Please share a story or example for each.

  1. Entrepreneurship is not as sexy as you think it is. Everything you see online is a highlight reel. I think entrepreneurs are getting more “real” about what it’s actually like to build a company but there is not a lot of information out there about how hard you’re going to have to work and the incredible weight you carry as you build a company. I have lost enough sleep for a lifetime, worked many 12+ hour days, and I see no end in sight. If you’re going to get started, make sure you’re doing it for the right reasons.
  2. It’s okay to ask for help. I have always been horrible at asking for help, and it’s definitely set me back as an entrepreneur. I think those that are comfortable asking for help from the start can build faster. Even if you’re a solo founder, you DO NOT have to figure everything out yourself. Build a network of people you can lean on. It’s okay to say you’re not okay… that’s still something I’m trying to pound into my own head.
  3. Hire carefully and fire fast. I have made a ton of hiring mistakes, and I’ve held onto employees longer than I should have. When I first started hiring it was very much based on gut feeling, and I should have been more process-driven, specific, and careful. Filling a role fast with someone who ends up being the wrong person is even more painful than leaving it open in the first place.
  4. You need a coach and/or mentor. I think a lot of people don’t immediately see the value of having coaches and mentors, but I think every great “player” needs a coach. Coaches hold you accountable and mentors help guide you away from the mistakes they’ve made… and with both resources, you’ll recover faster when you do make a mistake.
  5. It gets easier but it is never easy. When I started my first company 10 years ago, I felt like I was always waiting for it to be easy. Building a company never gets easy because the scale changes. That means your team gets bigger, your revenue and expenses get bigger, the wins get bigger and the challenges get bigger. Things that used to be terrifying and hard 5 years ago are easier now, but I truly believe that building a company is, and always will be, hard work.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

My big dream is to make an impact on the foster system as a whole, and especially in Milwaukee. I would love to see a lot more effort and money going to educating people about fostering, signing up foster parents, and fixing the system as it stands today. There are a lot of children and families that need help, and not nearly enough resources for them.

How can our readers follow you on social media?

I spend most of my time on LinkedIn; connect with me and my company below!

Me ☺

www.linkedin.com/in/thejackiehermes

www.twitter.com/thejackiehermes

www.instagram.com/thejackiehermes

Accelity

http://www.accelitymarketing.com/

www.linkedin.com/company/accelitymarketing

www.twitter.com/accelitymktg

www.facebook.com/accelitymarketing

www.instagram.com/accelitymktg

This was very inspiring. Thank you so much for joining us!

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