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Behind the Books: Conner Schryver's Formula for Small Business Success

Our success comes from building strong partnerships with colleagues who offer services that complement ours. We’re launching a series highlighting their incredible work and how they help drive value for our founders.



In 2018, Conner Schryver took a leap of faith and founded Bookkeep & Prosper, drawing on his extensive business administration and finance background. With experience managing back-office operations at a small private school, Schryver saw an opportunity to offer more flexible, streamlined bookkeeping services. Driven by a desire to align his professional goals with his growing family’s needs, Schryver transitioned from a stable career to full-time entrepreneurship in 2020, alongside his wife.


Bookkeep & Prosper has since become a trusted partner for businesses, helping them navigate financial challenges with clarity and foresight. In this interview, Schryver shares insights on overcoming obstacles as a new business owner, the importance of cash flow management, and the misconceptions about bookkeeping and accounting that business owners often have. He also offers valuable advice for aspiring entrepreneurs, emphasizing the power of securing that first client to kickstart success. Read on to learn more about how Conner Schryver is building a legacy of prosperity and balance, both for his clients and his own team.


Can you tell us a little about your background and what led you to found Bookkeep & Prosper?


I founded BookKeep & Prosper in 2018 while working as a business manager at a small private school, handling back-office operations, including accounts receivable, billing, payroll, and human resources. My background in business administration and finance made starting a bookkeeping business a natural fit. 


I was driven by the desire to create more flexibility in my work life, especially as my wife and I were planning to start a family. After our daughter was born in April 2020, we decided to leave our full-time jobs in June to focus on growing Bookkeep & Prosper full-time. We’ve never looked back, and it has allowed us to align our professional goals with our family life.


What were some of the biggest challenges you faced when starting your business, and how did you overcome them?


The first biggest challenge was finding clients. Initially, we leveraged our personal networks to spread the word. As we went full-time, we implemented a daily regimen of reaching out to prospects, which helped us gradually grow our client base.


The dedication paid off, and we began receiving referrals from satisfied clients. As we grew, we faced another challenge - transitioning from a solo operation to managing a team, which required balancing company growth with team development. We’ve worked hard to build a team that provides better service and flexibility for our clients and ourselves.


What are the most common issues small businesses face with their finances?


Effective cash management is crucial, so we focus on helping clients gain clarity on their current financial situation and project future cash flow to ensure they can meet their obligations. Small businesses often rely on their bank statements to gauge their financial health, but this approach doesn’t account for future expenses or missed transactions.


This can lead to inaccurate financials, which may result in higher taxes due to unrecorded expenses.


Can you describe a particularly challenging project you’ve worked on and how you successfully managed it?


One of the biggest challenges we face is catching up and cleaning up financials for new clients who are behind on their bookkeeping. These projects often involve a year or more worth of unrecorded transactions. We assess the timeline and urgency, then utilize our systems and team to quickly and accurately bring the books up to date. Once caught up, we continue working closely with the client to maintain accurate financial records and integrate their software to streamline future processes.


What are some misconceptions business owners have about bookkeeping and accounting that you’d like to clear up?


A common misconception is that once a bookkeeper is hired, the owner’s involvement is no longer needed. In reality, there needs to be ongoing communication to ensure all transactions are accurately recorded, especially if the owner uses personal accounts for business expenses.


Another misconception is that bookkeeping and accounting are the same. Bookkeeping involves daily record-keeping, while accounting, especially tax accounting, relies on accurate records to prepare taxes. Bookkeepers play a crucial role in ensuring the information provided to tax preparers is correct.



How do you stay updated with the latest developments in accounting and bookkeeping to provide the best service to your clients?


I stay updated through a combination of professional development and continuous improvement. Annually, I attend a bookkeeping conference that covers best practices, software advancements, industry updates, and new government programs. I also maintain membership and certification with the Digital Bookkeepers Association which requires professional development throughout the year. Our business is built on the principle of constant improvement, so we’re always seeking new ways to enhance our processes and better serve our clients.


What is the most important piece of advice you would give to someone considering starting their own business?


I believe the most important thing to do in your business is getting your first client. Having a product that’s good enough to sell is crucial. You may want your product to be better, but it’s important to get it to a point where it is sellable. Then, focus on getting that first client so that you can start to earn some money. 


There’s a book by Mike Michalowicz called “Fix This Next”, which discusses the hierarchy of needs in a business. The first thing you need is sales—if you don’t have sales, you don’t have any lifeblood for your business and you need to find a way to generate income. If you haven’t been able to do that yet, devote the majority of your time to getting your first client or subsequent clients to support the continued running of your business. After that, you can focus on the next need, but if you’re starting a business, the most important thing is having a product you can sell and then selling it right away.


What legacy do you hope to leave in the business world through your work with Bookkeep & Prosper?


I have a vision for our company to help our clients build and grow successful businesses so that they, their teams, and their families can all prosper. We aim to do this by providing clear insights into their financials so they can make informed business decisions.


You can’t make the correct decisions about your business without accurate financials, so we look at what’s happened in the past and also focus on forward-looking goals. Internally, I want Bookkeep & Prosper to be a business where people love to work, where we are truly a team. I want it to be a place that offers flexibility, allowing for a positive work-life balance. Additionally, I want our company to give back to the community and be a force for good, growing our profits not just to be profitable but so that we can contribute to the world at large.




If you want to get in touch with Conner, you can reach out to him at: conner.schryver@bookkeepandprosper.com


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