Jackie Hermes Shares How to Navigate the Downsides of Entrepreneurship

In this episode serial entrepreneur Jackie Hermes is here to share how you can view challenges as opportunities and navigate the not so fun parts of entrepreneurship.

3:25 – Jackie’s entrepreneurship story

Jackie became an entrepreneur in 2011 with a cookie company. She describes it as a good start, but it’s tricky to scale when you’re selling $5 bags of cookies. Taking the funds and what she learned from the cookie company, Jackie started Accelity in 2013. 

Accelity started with simply providing a service as a solo consultant, and has now expanded to 20 employees – and no office. As of September 2022, everyone is working from home. 

5:18 – The unsexy nature of being an entrepreneur

At the end of the day, if you’re the CEO of your business, the buck stops with you. This means you need to master the art of receiving feedback and problem-solving. 

It’s also a good idea to start training your mind to enjoy the process of growing. 

For instance: Once you hire a team, a lot of your time is going to be spent managing people. Doling out assignments, dealing with HR issues, making course corrections – all of those are now in your job description. But it’s part of growing. 

It’s not all flexible schedules and nice cars. You have to work hard to get there. 

7:34 – What should people who are just starting their business anticipate, in terms of unsexy entrepreneurial work?

In Jackie’s first six months, she had to really work to be on top of cash flow. 

There was also the matter of hiring a team: Cost of living is going up, and you need to make sure you’re hiring qualified people. That can be a time (and cash) consuming endeavor, but it’s worth it for the right employee. 

Always be working on your sales pipeline – don’t assume that a deal is closed until you have paperwork signed, sealed, and delivered. Sales is going to be an ongoing task (at the very beginning, the name of the game is networking). 

10:40 – The impact of LinkedIn

Jackie was a reluctant LinkedIn creator; she had to find a version of it that worked for her. She also notes that she’s playing the long game. There can be a hundred days of doing the groundwork, and then on day 101, you finally see the benefits. 

8:32 – Dealing with rude comments and choosing what to care about

It’s possible to care too much – at least about the wrong things. Rude comments on social media? Best to block and move on, so you can spend that energy productively on your own company. Jackie walks us through a tricky situation with a client, a situation that she had time and capacity to deal with because she decided what she cares about. 

25:49 – How Jackie structures her day as a business owner and parent

First of all, there’s not a strict, strenuous routine. She practices the “eat the frog” method, getting the most crucial task of the day done first. She also makes working out a priority for earlier in the day – but it’s not a set time, it’s when it fits in. Flexibility means being able to take advantage of quality time with her loved ones when the opportunities arise – and those opportunities are often not scheduled.

For Jackie, when there’s a crunch she doesn’t sleep less and work more. She can feel an impending burnout, and would rather slow or shut things down than push too hard. 

31:11 – What to do if you’re an entrepreneur who’s tired of the unglamorous side of running a business

A good first step is to acknowledge that you’re not the only one feeling this way, and it’s a lot of pressure. 

It’s okay to say out loud that you’re not doing well. Find someone that you can trust, and talk things out. 

Another good thing to know is that life works in seasons. You are not meant to work all 60-hour weeks. There will be some weeks when you have a really high capacity, and other weeks when you need to cut back and rest. It’s seasonal. You can either fight that, or lean into it. 

About our guest:

Jackie is the founder and CEO of Accelity, a marketing agency that helps B2B software companies grow faster. She’s also a mom of three, a startup mentor, the founder of Milwaukee's Women Entrepreneurship Week, and host of the podcast The Art of Entrepreneurship.