William L. Coney Blog: From Wall Street to Entrepreneurship: 6 Hard Lessons Learned

The transition from the corporate world to entrepreneurship is jarring for anyone who takes the leap. The work, structure, and indicators of success are different in many ways.

Things you became adept at while working at a company—like keeping your boss happy and navigating office politics—lose their utility when you’re on your own.

I can attest to this dramatic change after I took the leap. After graduating college, I spent several years on Wall Street, first at a large investment bank working on M&A for large corporate clients, then as a private equity professional helping invest hundreds of millions of dollars in private companies.

It was an exciting environment with a steep learning curve. However, having grown up in a family of small business owners, the pull of entrepreneurship strengthened as I grew older. After several years in the corporate world, I realized it was never going to get easier to make the switch.

Leveraging our financial skill sets, my partner and I started Harper Partners, a tech-enabled factoring company that helps innovative B2B businesses and startups fund their working capital. The transition from a white-shoe Wall Street firm to the near absolute freedom of entrepreneurship required enormous adjustments in all aspects of my life.

After thinking back through my experience, I identified six key lessons, which are applicable to anyone considering the employee-to-entrepreneur path.

1. Get used to a lack of short-term feedback

This is a major mental hurdle that many entrepreneurs—including myself—struggle with. As students and then employees, we receive short-term feedback constantly. First your teachers, then your managers tell you how you did on each test or project. Adjustments are easy when you know what you did wrong and how you can improve.

Unfortunately, this doesn’t exist in entrepreneurship. No one is going to tell you what you did wrong unless you know how and who to ask.

To address this problem, I found mentors who had been successful in my company’s area of commercial finance. Having someone experienced to bounce ideas off of is crucial so you don’t waste time and resources. I also learned to test my ideas and get feedback from existing and potential customers. As an entrepreneur, your customers are the closest thing you have to a boss, so speak to them often!

2. Set aggressive schedules and stick to them

When you’re an entrepreneur, schedules can quickly become warped. The sudden sense of freedom can be simultaneously intoxicating and terrifying, especially if you come from a hierarchical environment like I did.

However, there’s a reason why building a business is one of the hardest things you can do. Though no one is telling you about deadlines, they exist. After all, the market is shifting, your customers are demanding, and your competitors are hard at work.

Set goals and invest in a scheduling system that will keep you progressing toward them. I use Asana, but there are a host of other excellent scheduling tools on the market.

Scheduling must also be applied to your organization as it scales. At Harper, we have Monday morning meetings with the team where we discuss initiatives, sales pipeline, closed transactions, and general business matters. My partner and I also have daily check-ins to discuss more immediate matters.

3. Don’t be afraid to get your hands dirty—it’s required

A benefit of being an employee is being able to focus on your role and not worrying about anyone else’s. That luxury doesn’t exist in entrepreneurship. You will have to be involved in every aspect of your business.

As a founder, you will touch sales, marketing, product development, customer service, accounting, fundraising, and more. Even if you have partners or vendors handling some of these responsibilities, inevitably your roles will overlap.

It’s unwise to outsource business functions (even if you don’t like them) before you know how to do them yourself. That means setting up your accounting before getting a bookkeeper, or understanding marketing even if you’re focused on product development. We all have comfort zones that we settle into naturally. Be prepared to constantly challenge your boundaries as an entrepreneur.

4. Customer acquisition will be harder than expected

This is the biggest miscalculation new entrepreneurs make. Many think that building a great product is all that’s required to bring in users.

Acquiring customers is always harder than expected. A good approximation of the cost to acquire a customer (“CAC”) is to take the industry leader’s cost of customer acquisition (annual sales and marketing spend/new customers added per year) and multiply that figure by five.

That may seem high, but no one knows about your company, and frankly, no one cares until you make them care. The CAC of the industry leader is so low because they’ve already established a brand. Much of their new business likely comes from word of mouth, which solves to a CAC of $0.

5. Learn to relax and recharge

Finance professionals are known for their tremendous work ethic—a characteristic many entrepreneurs share. However, with aggressive personalities that push themselves hard, the possibility of burnout exists.

This is especially true in the first couple years of a new venture where it always seems like there are a million things to do. In this stage, the boundaries between work and personal life can blur. However, founders would do well to remember that entrepreneurship is a marathon, not a sprint.

Having only known a culture of working around the clock during my time on Wall Street, I could feel myself wearing thin during the first year of running my company. I wore the long hours and late nights as a badge of honor. But this non-stop life was wearing me down. I was losing enthusiasm for my company and seeing a decline in personal health.

I realized if I was going to last I needed to set boundaries and learn to recharge. I blocked off time four days a week to go to the gym, started using meditation apps, and made sure to prioritize time with my friends.

6. There are many ways to make a living

I didn’t realize it at the time, but I lived in a Wall Street bubble. You’re so focused on your work that you’re rarely exposed to how other business owners make money.

Sure, my teams helped companies raise money and invested in them, but those were arm’s length transactions. They were not operating experience. Additionally, we mostly dealt with big, established companies. There are millions of entrepreneurs living very fulfilling and prosperous lives running businesses much smaller and less prominent.

Once I left the bubble and allowed myself to explore, I began to see the countless niches entrepreneurs inhabit. Maybe you need to cut expenses for a couple years as you develop your idea. But, there are so many opportunities for bright, hardworking individuals.

Though it may not look like it if you feel you’re in a corporate bubble, the world is indeed a very big place.