A Founder’s Journey Requires Handling a Constant Pressure To Perform With Jeffrey Fidelman

A Founder’s Journey Requires Handling a Constant Pressure To Perform With Jeffrey Fidelman

VENTEUR spoke with Jeffrey Fidelman, who manages a 40-person management consulting firm parallel to being a freelance CFO, about his entrepreneurial journey. Fidelman’s firm focuses on providing strategic services to early and mid-stage companies. As a consultant/freelancer, he has acted as an interim CFO/COO for 100+ companies and funds. A few highlights of Jeffrey's career outside consulting include being a partner at a VC fund, banking with Morgan Stanley and HSBC, and co-founding a real estate brokerage. Jeffrey graduated cum laude from Harvard University.

The Journey

The entrepreneurial journey is one of self-discovery. What have you learned about yourself while building your business?

I have learned that patience is key when building a business. Relationships take time to develop, and there will be setbacks. But if you remain patient and keep working toward your goals, things will eventually fall into place. Luck is not a factor–it's all about opportunity meeting preparedness. And only with patience can you wait for the right opportunity to present itself.

The entrepreneurial journey is often lonely. Have you experienced loneliness as an entrepreneur? 

Yes, I have experienced loneliness as an entrepreneur. The journey can be lonely because you often have to pave your path to accomplish your goals. The common trait amongst entrepreneurs of being lonely reflects their need to spend more time thinking and less time doing. To overcome this loneliness, I have made sure to surround myself with supportive people who understand my journey. I also make sure to take time to relax and recharge. This helps me to stay focused and motivated on my goals.

What role has intuition played in your success as an entrepreneur, and why do you think this is the case?

Intuition has played a considerable role in the success of my business, myself, and as an entrepreneur. The only difference now from when I started my career journey is that I'm able to and have the confidence behind not only having an intuition but being able to lean into it and figure out a way to either monetize or take advantage of whatever my intuition is telling me to do. 

For example, if I have a gut feeling that a particular business move will be successful, I'll go for it and trust my instinct, even if it's a risk. So far, this has paid off big time and has helped me get ahead in the entrepreneurial game.

The Psychological Warfare 

Entrepreneurs generally sleep less, work more, and let their health slip. This combination, combined with loneliness, often results in insecurity, self-esteem issues, and low self-worth. Have you experienced any of these issues as an entrepreneur? 

Yes, I have experienced all these issues as an entrepreneur at one point or another. I try to keep as much balance as possible and work hard to maintain a healthy lifestyle, but it is a challenge. Imposter syndrome is something that many entrepreneurs feel, especially when starting. It can be easy to compare yourself to other entrepreneurs who seem to be more successful or have more experience, but the reality is that we all have different paths. 

However, there are common denominators that connect us all. I think that is one of the things that I like about being an entrepreneur–it allows me to connect with other people going through similar challenges and experiences.

What is the most unrelatable part of being an entrepreneur, how does this impact your mental health, and why?

The most unrelatable part of being an entrepreneur is the constant pressure to perform. This can impact mental health by causing stress and anxiety. It can also lead to burnout if entrepreneurs do not care for themselves. The constant pressure to be "on" can also be isolating, as it can be challenging to connect with people who do not understand the job's demands. 

Many people don't understand that you are losing money if you're not making money as a business. It's not the same as a 9-5 job where you can clock out at the end of the day. For entrepreneurs, the work is always there and can be overwhelming. On top of working more than the average hours during a workweek, working 24/7 during weekends, holidays, and even in the middle of the night is very common for entrepreneurs. 

However, I'd say that the mental health impact for entrepreneurs can be very significant since the job is demanding and all-consuming. If they don't take care of themselves, it can lead to severe problems down the line.

The Mistakes

What are three mistakes you made early on as an entrepreneur, what did you learn from them, and how can others avoid them?

1. Overextending Myself

A mistake I made early on as an entrepreneur was trying to do everything for everyone. I learned that it is crucial to focus on what you do well and eliminate anything that isn't essential. This will help you be more successful in the long run. 

2. Not Assessing How Passionate Someone Is About the Core Principles of My Business

Another mistake I made was not empowering people and trying to teach them to do things they may not be interested in or qualified for. Finding people passionate about what you are doing and who you can empower to help you achieve your goals is essential. 

3. Not Being Proactive With Organization

A third mistake I’d mention is waiting too long to organize operations. I would encourage entrepreneurs to set up their billing, payment, communication, and other infrastructure as early as possible to avoid problems down the road. To avoid these mistakes, focus on your core offerings, empower those around you, and get your operations in order from the start.

What are three things you see that are often overlooked by entrepreneurs you encounter, and how can other entrepreneurs be aware of these things from the beginning?

From my experience, entrepreneurs often overlook the importance of timing, payments, and corporate structure. 

1. Timing 

Timing is crucial for everything from fundraising to product development to launching a new initiative. If you don't give yourself enough time to complete a task or reach a milestone, it can bite you later. 

2. Payments 

Payments are another critical part of running a business. You need to be able to accept payments from customers and clients, and you shouldn't let the process of accepting payments be a barrier to doing business. 

3. Corporate Structure

Finally, the corporate structure is often overlooked but can significantly impact a business' success. Make sure you speak with an attorney to determine the best corporate structure for your business.

Jeffrey Fidelman

The Successes

What are three seemingly insurmountable obstacles you've faced as an entrepreneur, and how have you overcome them?

1. Overcoming Self-Doubt

When you're first starting, it's easy to doubt yourself and your ability to succeed. I overcame this by surrounding myself with people who believed in me and my vision and staying focused on my goals.

2. Making Tough Decisions

As an entrepreneur, you often have to make tough decisions that can impact your business significantly. I've overcome this by being as informed as possible, staying true to my values, and consulting with others when needed. For example, hiring or firing people is always a tough decision, but it's one that you have to be prepared to make.

3. Dealing With Failure

Failure is inevitable in business, but how you deal with it is what counts. I've overcome failures by using them as learning opportunities and getting back up and trying again.

The Advice

What three key pieces of advice would have made your entrepreneurial journey more manageable, and why?

1. Keep It Simple and Focused

Many entrepreneurs try to do too much, which can lead to burnout and becoming overwhelmed. It is essential to find your niche and focus on that rather than trying to be everything to everyone. This will help you become an expert in your field, which is the next piece of advice.

2. Become an Expert in Your Field

This may seem like common sense, but it is essential to focus on becoming an expert in your chosen field. This will help attract clients and investors looking for someone with your specific skill set.

3. Understand Personal and Business Finance

Before taking on any capital, it is crucial to understand all of your options and the associated costs. This will help you make the best business decisions and avoid financial trouble down the road.

What is the most significant difference between how an entrepreneur sees their career path versus how an employee at a company sees their career path, and why?

The most significant difference is that an entrepreneur is typically more focused on the long-term goal, while an employee generally is more focused on the short-term goals. An entrepreneur is also more likely to take risks, leading to higher rewards (but also higher failure rates). Finally, an entrepreneur is typically more independent and has more control over their career path, while an employee is more reliant on their employer.

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