How My Inner Reflection Sparks External Action

It’s Sunday. I opened my Bible app. I read this verse, “Many are the plans in a person’s heart, but it is the Lord’s purpose that prevails.”

When I read it, I thought, “What if a person has no plans?”

Seasons change

A conversation with my twenty-eight-year-old son got me thinking about my life. His twenties were about establishing his career, building an early professional network, and increasing his income. This led to subsequent upgrades to his living conditions, from two roommates to one roommate. And now he is thinking, “At the end of this lease, I might want to have my own apartment.”

This change does not come easily. It is fraught with emotion because of his close relationship with his roommate, his lifelong best friend. But the more profound struggle is the reality of changing seasons. He is nearing the end of his twenties and moving into his thirties. He must release the life he is living to open himself up to the next season in life.

What about me?

After listening to him and feeling the emotion resulting from his potential change, I realized I was going through the same thing. The difference is his upcoming season is all about building the next phase of his life. He is entering his thirties. I am entering my seventies.

The next step in his career is to lead others and help them be successful. Maybe discover the life partner God has picked out just for him. Buy his first house. Get married. Wrestle with the prospect of having kids. Raise kids. Find a church and school community. Meet new people at work and in the neighborhood. All of this describes a season focused on expansion. Life is getting bigger.

Then there is the season of the sixties.

The sixties feel to me like a decade of wind down. I discovered my interests were changing. I was all about finding and working with entrepreneurs in my forties and fifties. Helping them achieve their dream of starting and building their own company and, along the way, finding good investment opportunities.

These investment opportunities created a new business partnership. A partnership where the entrepreneur’s goals and skills matched well with my goals and abilities. This allowed both of us to add value to the newly created entity. It was a great ride, lots of fun, and financially rewarding.

Then, my sixties came along. I realized I still wanted to help entrepreneurs but was losing my interest in investing. I didn’t want to be as involved in the new business as I was in the past. I was interested in being available, but differently. I wanted to offer situational advice rather than ongoing strategy or operational advice. In fact, as I look back, my interests moved more to life advice versus business advice.

I was making a seasonal change from my fifties to my sixties. And this new season was focused more on helping entrepreneurs in their next step in life versus their next step in their business. In effect, giving entrepreneurs a perspective on where they are headed in life by detaching their identity from the company. And that is why I started my blog over five years ago.

The Paparelli.com Blog

The blog was a way to share my thoughts and what I learned in a life dedicated to working with entrepreneurs. Share what I had known that worked and didn’t work when building a business and a life. I wrote to tell my story and the stories of the entrepreneurs I worked with over the years. People found it interesting because it hit on business, life, and faith themes.

But this blogging was costing me money. I went to seminars to discover how to become a content creator. I hired an editor to help me get the writing right and to coach me. I had a web editor create the paparelli.com site so it was accessible, organized, and readable. And then I had to pay to maintain and distribute it. I decided I needed a business that complimented my writing that could offset the cost of paparelli.com.

My new business: coach

I decided to become a coach. I had no idea what that meant, but I thought this was a logical next step in life. So I called a few entrepreneurs I was close to and asked them about it. Two of them jumped right in with me. So now I was a coach. I must be. People were paying me to do it.

The initial excitement of the new coaching business propelled me forward. I quickly learned this was going to be hard. These people wanted me to show up and be available. My time was no longer my own. I was on their time and needed to be available when it was convenient for them.

I also had no real vision for this coaching. So I coached them to make their business better.

I asked a friend who is a coach for some tips. He told me, “You are not a coach. You are a business advisor.” As we discussed this, I knew he was right. Whenever I talk with an entrepreneur, my thought immediately goes to how to improve their business. It is easy for me to engage with an entrepreneur at this level.

But I wanted to do life coaching. I wanted the coaching to support the blog.

I had difficulty transitioning from business advice to life coaching. And there were two reasons for this. One, business advising is just easier to get to. Every entrepreneur wants to talk about growing their business even faster. And two, business advising is far less threatening to the entrepreneur. It is about the company and not the entrepreneur.

But I had a problem. I ran out of steam really quickly in my coaching. My business advising resulted in short-term engagements due to short-term value being delivered. I am an excellent strategy advisor for entrepreneurs. I understand startup challenges, early-adopter markets, distribution channels, and entrepreneurs. But I am not the best at how to accomplish the strategy.

In short, I am a great "What" advisor but not a very good “How to” advisor.

Then, I learned the most successful business advisors had process-oriented methodologies. I didn’t have that and wasn’t interested in developing it. After all, I didn’t set out to do business advising. I wanted to help entrepreneurs take the next steps in life.

And finally, I learned that great life coaches have a real bent toward human resources and behavioral psychology. This I do not have. Never have and never will. It is not me, and I’m not interested. Is it valuable? Yes. But just not an interest of mine.

Where did the coaching business go?

At this writing, I am scheduled for lunch tomorrow with my last entrepreneur coaching client. He will tell me at this lunch that he no longer needs my services. And the reason is simple.

I ran out of value as a business advisor. He is now running a good business. In our last meeting, I focused entirely on him and his life. It was an exciting look forward into who he might become and how that will probably increase the business's overall value. But there was clear risk in this approach for the business and him.

After some thought, he decided to let me go. He doesn’t want someone in his face pushing him to change his life. He likes what he is doing and wants to continue doing it. And part of me doesn’t blame him.

Choosing the entrepreneur life is very much about freedom. The freedom to be yourself. The freedom to freely exercise your values. The excitement of surrounding yourself with people who value you and what you believe. The thrill of pursuing a shared vision together. And finally, the freedom to run your business how you want to run it so you can live the life you want. Even if it means the value of the business won't be optimized.

The coaching business is a full-time job.

I don't want a full-time job at this season of my life. I am sure if I’d leaned into the coaching business over the last three years, I could have made a living at it. I wasn't willing to commit to learning a new business. To commit to the market pivots. To commit to the patience it takes to endure the compromises for success. To commit to the promotion, networking, and methodology building to make it a real business. No. I didn't lean into it, and it became more of a distraction in my life than an interest. There is that word again, "interest." I am continuing to search for my new interest.

So I am not a coach. What am I?

I largely kept the coaching gig quiet while remaining positioned as an angel investor. But this identity is not matched by a growing interest. But letting go of my identity as an active angel investor has been a real struggle for me. After all, I've been doing angel investing for almost thirty years. I was asking myself, "What am I in our startup community if I am not an angel investor?"

Here's what the transition looked like while I answered this question.

I kept investing. I did not want to lose my brand, my relevancy, my impact. But I was losing interest. And this loss of interest combined with my trying to hold on to an interest that was slipping away resulted in poor results. I was making investments recklessly. I went from lead investor to passive investor. Another way to say it is, I knew what I needed to do to be a successful angel investor, but I didn't do it. I just wrote checks. This is a formula for failure. It is like going to a racetrack and betting on a horse because he has a catchy name rather than doing the research on the horse's last race and workouts, today's track conditions, and his competition in this race.

I finally faced this harsh reality halfway through my sixties. I decided to simply do follow-on rounds to current investments that had momentum. And now, at sixty-eight, even that has ended.

But something interesting has happened since the pandemic.

In April 2020, when the country shut down and the economy shut off, I started something called "Zoom Chats for Entrepreneurs." Every Wednesday from 9-10 am, I would host an open call on decisions entrepreneurs needed to make that week. These were decisions forced upon them by the pandemic. The problem I solved was to give these entrepreneurs a forum to discuss it, to see what their peers were thinking and doing.

At the end of 2020, over the Christmas-New Years holiday, I decided to pivot to a new model. Entrepreneurs had figured out their new operating mode in the pandemic. The problem I was solving went away. No more Zoom Chats for Entrepreneurs.

I learned in doing these thirty-minute interviews that these entrepreneurs had so much more to offer to other entrepreneurs. So I decided to do long-form interviews of successful entrepreneurs. I created a YouTube Channel and the Paparelli Podcast.

This year I have published 40 interviews.

The idea for these interviews also came from helping entrepreneurs over the last thirty years. Most entrepreneurs in their first meeting with an angel investor, expect a thirty-minute meeting. They open their laptop and start walking through the investor PowerPoint slide deck. I would always stop them as they began to open their laptop. I would say, "Let's just talk for a while and get to know each other."

This led to understanding them, their business, the timing, and the opportunity. It also was always a two-hour meeting. But at the end of this time, we really got to know and appreciate each other. We built a relationship. I liked that. It was a good use of my time because it was a good way to serve the entrepreneur.

So now, when I am doing these interviews. I know I am doing what God wants me to do. I know it because I see the impact it has on the entrepreneurs being interviewed and my audience of entrepreneurs. I also know it because of the fulfillment it gives me.