The Pros and Cons of Working with Startups with Jessie White

Jessie has a background in education and actually worked as a history teacher. One day in her third year, she wanted to teach some new classes and was given a flat refusal from her boss. At that point, she realized her days as a teacher were numbered. She stumbled upon Bookkeeper Business Launch on the Penny Hoarder and it seemed like a good fit. She enrolled in the course in August, launched her business in October and got her first client in November.

[5:25] Before jumping into bookkeeping, Jessie was considering other jobs including different teaching positions. Once she learned what bookkeeping really is, it checked all her boxes. Going through the modules in the course was challenging initially but she benefited a lot by discussing the contents in the modules with her husband.

[8:00] Jessie’s first client was a startup that just needed some help with their setup. She was close enough to actually meet in person so she drove to her place to do some training with her before landing her as a client. She now has 15 monthly clients with a few others who require different services.

[10:00] The first client and the majority of the subsequent clients were mainly found through LinkedIn. Building relationships with a couple local CPAs has also been helpful by referring clients and offering help. You never really know where the most valuable relationships will come from.

[12:45] The business of bookkeeping can become a monster if you let it, so Jessie books time every day to make sure that she has time to herself. Even with that challenge, Jessie considers herself completely unemployable at this point.

[14:20] There were three major struggles that could have ended Jessie’s business. One of her lowest points involved getting fired by her second client. There are many reasons to quit a business but you have to remember why you started it in the first place.

[16:25] In terms of vision, Jessie would like to move into more of a manager role. She would like to be able to work more with the clients and help them grow.

[19:00] Jessie loves working with startups but it can be difficult because they have so much on their plate. It’s a challenge to know what to charge and get their attention because they tend to be overwhelmed. It’s a lot easier to help a business grow in the beginning than it is to jump into a big business that has never done their books at all.

[20:50] It’s very important to work with the right kind of startups. The ones with no money and no direction can be a major headache. The best kind of startup with whom to work are the ones with funding. If they don’t have money because they’re bootstrapping, it's probably going to be an issue. Vet and qualify your potential clients on the front end based on their capital structure and business model.

[25:25] Most of Jessie’s clients reach out to her within their first two years of business and the majority of them don’t really do much beyond a box of receipts in terms of bookkeeping. The optimal time is probably around the one-year point. That’s when it will be obvious if the business model is sustainable.

[28:00] Jessie’s niche is health and fitness but it really comes down to the personality of the entrepreneur that she’s looking. It’s important to write down the specific attributes of your ideal client and what motivates them. Start with your favorite clients and what they have in common.

[31:20] Based on your avatar of your ideal client, think about who already has their attention. For Jessie that means CPAs and people in the banking industry. That can also mean attorneys, podcasters and authors as well. Those are the people with whom you want to establish relationships. It doesn’t take too many of those to start getting clients. Keep in mind that the best way to get a referral is to give a referral.

[35:30] You should try to get in the frame of mind of the referral partner and what they need from the relationship.

[36:40] Jessie could also get a list of recently established business owners and create a piece of content to serve their needs then put that in front of them.

[38:10] Jessie should strive to be known as the Startup Bookkeeper. It won’t be a rapid process. but by creating content that actually helps her avatar achieve what they are trying to accomplish, she can become a trusted authority. Most of the people with whom you get connected will never pan out, but the ones that do work with you will pay off.

[40:20] Startups have a particular set of challenges. By creating a lot of content and doing the work upfront, Jessie can create a tribe that will be much more inclined to become her clients when the time comes.