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The Lonely Entrepreneur

Going it alone is not a strategy

The road is long and winding and best explored with someone who knows the way.
The road is long and winding and best explored with someone who knows the way.

Waking up to another bounced check notification I felt the anxiety building up in my body and it was a mixture of anger, regret, defeat and fear. I had ignored the signs that this was coming, I wanted to believe so badly that this was just a standard moment in a start-up’s lifecycle. With an incredible year of success, profitability and an outlook of magnitudes of growth for the new year, this business was bulletproof. Or so we thought. Or so we were told.

Just a few months prior I was at the wine shop on the corner of 68th and Columbus buying up too many bottles of champagne to cheers to a new round of investment, a critical new hire and an idea for a new technology that was going to turn the entire industry on its head.

Pop…fizzz…clink.

The 6 of us cheers with overflowing glasses and patted each other on the back for our wins and our relationships and our ability to turn $0 into $2.5MM in less than 16 months. Definitely something to be proud of and we were all part of it, each of us lending our expertise and willingness to get the job done. And we did it for our leader, a person exuding charisma and generosity. You wanted to move mountains for him. We were drinking his Kool-Aid…

Never mind that one moment, where he quickly hung the phone up on a prospecting call and turned to Me and said, “oh they were just looking to steal our ideas, you need to be careful of the sharks” – Or the time on the call where he seemed to switch from light to dark in a single minute and accused the already committed client, of “Trying to get Dom Pérignon at Chardonnay prices” – Or the time that we had to make the hard phone call revealing the entire plan we presented, and that they had already allocated money for, a plan that felt too good to be true, was in fact, too good to be true and was never going to happen – Or that time that I was put on the call to beg for the money because we over-promised and we, unbeknownst to me, couldn’t run the campaign without it – Or the time, for that same partnership, that I had to take the call where they were pulling the entire plan because what we were asking was ‘shady’ and not standard in our industry…

Want me to keep going? Because I can. When I would tell these stories to my industry friends, many of them would gasp. Why was I still there? Why wouldn’t I leave and go somewhere where the leader wasn’t such a paranoid hot-head?

I would like to go back and ask myself that, too.

I know intelligently that I believed so strongly that this was MY company and this was just another ZANY CEO that had his many odd moments and they were mixed in with all of these fun, playful, exciting moments that it dulled what was probably worth a little further investigation.

Imagine, they dangle this idea that the company will exit for $14MM in less than 18 months and with my equity I could make nearly $1MM and then I could be out of the rat race, and I could tell all of my friends how amazing it was to be part of an exit and I could keep up with all of my amazing friends who were already part of an exit. Another colleague and I had already picked out our Cartier bracelets and the exact date that we were going to buy them. It was a bulletproof plan.

Never mind the late guarantees, the bounced checks, the commissions that came nearly one year late. Never mind that we had very little transparency into what was coming in or what was going out. Margin? 40%? 70%? Never mind hiring the sales director, that I managed, who was making $20,000 more than I was – but He Was going to ‘make good on that’ eventually. Never mind that He left the paper payroll checks face up on our desks so everyone could see how much more my subordinate was making than me.

The first bounced check was brushed under the rug as an administrative error. “Switching payroll companies, so there will be a 2 week delay”. Does that sound right to you? Would an international payroll company delay employee paychecks for that long? In my mind at the time,  it made good sense. I will just wait longer. Then that check bounced. A paper check was handed over. That check bounced. Fees were adding up but “No worries, I will put those fees back into your next paycheck.” Ok, no problem, these are just growing pains. 

Growing pains that lasted for 6 months and ultimately ended up in $0 pay. Not without some finagling first. First we got the I.O.U. with interest and then the payment plan and then the revised payment plan. Then we were asked to do a team sales call. Being on that call felt like sitting in a bowl of tapioca pudding, tense, awkward, tears, no one wanted to be there. I could feel how everyone just wanted to hide under their desks. 

Never mind some people were getting paid because “they would never tolerate not getting paid.” Never mind that some people were “committing to the next iteration of the company, 2.0, are you on board with us or not?” Never mind that “I don’t have a plan, I don’t know what’s going in and out, I don’t know when I can pay you, but you will get paid.”

And I still believed. I still held out. The interest being offered was going to add so much more money to my bottom line! I was going to get it all in one awesome lump sum! I was going to be rich! How much more could I lie to myself before I admitted defeat? How much more was I going to let this person continue to abuse the power he had over me? How much longer was I going to willfully hand over my power? 

2 more months! That’s how much longer. After sitting on the floor of my apartment after a massive panic attack I was faced with a choice that was so clear to me. Fish or cut bait. Shit or get off the pot. You’re burning daylight. Believe this is really happening to you. You haven’t seen a paycheck in 5 months. You don’t have a job lined up. You don’t know where to go or what to do but you MUST do something. Decide!

I had always been able to ‘figure it out’. Looking back, I never really ever ran out of money, I never didn’t have a place to go, I never didn’t have someone in my corner with a hot meal and a job referral. Sitting on the floor panicking wasn’t getting shit done. And I get shit done. What were my resources? Who did I know? What could I do right now? It’s incredible what your mind can come up with when you are either desperate or inspired. 

Through that clarity, I switched my thoughts back to him and this situation that was just surreal the further I distanced myself from it. What the hell happened? Looking back at those ‘red flag’ moments, I can see pretty clearly what the hell happened. 

He was in total fear. He acted totally alone.

Yes, we were there, all 6 of us, we were available and willing to step up for anything needed. But there was no board, there were no advisors, there was no oversight but him. Sure there was a consultant here and there but there was no respect and there was no real transparency with these temporary people. I heard about an advisor overseas, I heard about a mastermind. There was a ‘lead investor’ that stopped by here and there. And the rest is a mystery…

Since then I have stepped fully into my coaching career, a side hustle that I had going for a few months prior to the implosion. I’ve learned what fear can do to a business owner. Combining that with acting alone in almost all endeavors is a recipe for disaster. You are so busy plugging the holes in the boat, with no help and no time for solutions that pretty soon the dang boat will sink. Even a small staff and a point solution requires oversight, new ideas, resourceful help when it comes to effective management and finances. We were building the plane as it was taking off, that is not a one man job. 

There were moments of total paranoia that I always felt were fairly natural when you are building a business, people are going to steal my ideas and then change the industry, make the money and leave me in the dust. Honestly, just by thinking that would happen, he made that happen. It didn’t even need to fully materialize in the real world. Because that idea was so real in his head, the final outcome happened, just not in the exact way he thought. Instead of someone else doing it to him, he did it to himself. And to us. 

That paranoia manifested in a lot of calls to lawyers, can’t imagine that’s not expensive. And led to not being honest about some of the plans that we put together that were signed off on and paid for. Paranoia can lead to wishful, magical thinking. Paranoia is magical thinking. If people are magically after us, then it’s also possible in the brain of someone paranoid, that some major problem could get magically solved. No need to intervene, let the invisible magicians do their work! 

I can’t blame him. I had my own invisible magicians in my head as I sat on my apartment floor for 2 months gritting my teeth and hoping for a miracle. Miracles do happen. Just not on their own.

Acting alone as an entrepreneur leads to some insane thinking. You’re in your head. In your head things are distorted. Things are bigger or smaller or wider or deeper than they are out here in reality. Its when we share what’s in our head that we get it sorted out and in it’s right sized box. When there is no one to share it with it stays in its distorted state. And how lonely that must feel to have no help. To feel like you have no help. 

And loneliness sends you deeper into your head and the paranoia sets in and then you can’t share because you don’t trust. All the while still believing there is a chance that things will turn around. But nothing changes, if nothing changes. To thrust yourself out of chaos, you can’t be using the same thinking that also got you into the chaos. That same thinking that sharing any nugget of yourself is going to get you ripped off and left for dead. That same psyche that got you stuck cannot get you unstuck. You cannot do this alone.

Imagine how hard this must feel? How much shame is associated? How much fear is setting in? I know these feelings well. I have dealt with shame, denial, fear, guilt and regret. On a large scale. For years I held onto a secret that only a few people knew and honestly, a few people benefitted from. But I was full of shame and neglect for myself and others. It was cardinally, wrong. And the only way for me to move past it was to share it. To put light on it. And to seek my own forgiveness about the situation and subsequent events. 

How can I apply this same forgiveness to him? How can I forgive someone who reduced me to rubble, a person who spent her entire life savings, cashed in her 401K, maxed out her credit cards and still left with nothing? How can I find space to forgive? Because I am still alive. Because I learned valuable life lessons. I learned to listen to my intuition. I learned to let go of how societal ideals about money can cloud your judgement. I learned to let go of what other people think of me or that I need more money or more status to be loved. I let go of what failure really is. I now trust that I am taken care of. I am always taken care of. That life is working for me. That life is working through me. And because I believe these things, I can have compassion for him.

I have compassion for a person who thought he was doing his best. He was doing his best, because that is what he did. I will no longer argue with what is. Who am I to say that this wasn’t a lesson for him, for me, for the 4 other people. We all learned the power of failure. The power of decision making, the power of a team. We learned to stick together. We learned to be authentic and transparent. We learned that even if you take away our money, all of our money, you cannot take away our ability. Our willingness. Our courage. Our compassion. Our sensibility. You cannot strip us of experiencing joy and kindness, empathy and forgiveness. 

Sure, for a while my whole body was filled with anger and hate for him and what happened. But that’s not how to live an extraordinary life. And my life’s mission is to live an extraordinary life. And that’s it. That’s the goal. Does being resentful and vengeful help you live in a beautiful state? No. Do I need to live in a beautiful state all of the time to live an extraordinary life? Yes. So I let go of resentment and fear. I let go of not sharing my story and my needs. I let go of hiding and feeling shame. I am who I am. And I love it. I went through this because it’s preparing me for something so big that this is going to feel like a tiny pin prick in comparison on my timeline. 

And I hope this is how he feels too. If he can look through this moment at the other side, there is literally nothing that can stop him from becoming who he truly wants to be if he can overcome this moment in his life. And please, we can all overcome. You’ve heard the stories. 

Jordan Belfort, Martha Stewart, George Forman, MC Hammer. These people ‘lost it all’. They did some bad things. Some went to jail. And they came back stronger than ever and brought value to people’s lives by sharing their stories.

The ultimate lesson that I take from this moment in my life, a moment that is still not rectified at the time that I am writing this, is ask for help. There are so many great people who have done what we are doing and were once where we are. They want to help. Humans want to help each other. We are a pack. I want to write my story to help you. To show you that you can overcome. To show you that you don’t have to operate alone. 

This is a cautionary tale to not act alone. Create a council of peers that you can share ideas and problems and solutions. They need you too. They need your stories and your strife. Get a coach, a trainer, a mentor. Join a mastermind. Share yourself. The more you share the more you get back. Read the stories, in each success story there are at least 10 failure stories. 

Walt Disney was fired for not being creative enough. He bankrupted a company. He was turned down 302 times before someone believed in his idea for Disney World. Imagine a world without Disney World?! I don’t even want to think it! 

I have a council. I have a program. I have a routine. These are the tools I use to stay out of my head, to get into the solutions and ultimately to trust myself that I GOT THIS. 

Follow me @sarajoymadsen on Facebook, Twitter and Instagram

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