I quit my day job 1 year ago

Well its been almost a year since I left my day job in pursuit of greener pastures working on personal projects. I believed in making the move that I could sustain my desire for meaningful work and have the necessary flexibility in my day to day to focus on the people and things I really care about, namely my family, recent passions like guitar and friends I wanted to spend more time with. I thought I would officially come clean and tell you that I haven’t achieved what I set out to do with a covert agenda of ‘marketing’ the things I am working on and hopefully solicit some feedback.

Lets start at the high level:

1. Am I spending more time with my family? - I am a permanent Uber driver for my kids and I’ve freed up my evenings if I’m not driving.
2. Am I playing more guitar? - No. I had hand surgery and that messed me up
3. Am I seeing friends that I want to see more often? - Yes, or at least some of them.
4. (and now the big one) Am I spending more time on projects that sustain my desire to do good work? - For a while yes, unfortunately things didn’t go as planned.

Its this last piece I thought I could break down for you in some detail thinking it may be interesting enough for you to ask me questions.

First off, part of doing meaningful work is to work with people that you trust, that inspire you and that you believe can help you succeed. I am doing that. I lean on my partners personally and professionally to smooth out the waves and to that end, I’m thankful that I get to do that.

One of the projects I created for myself was to completely replace my salary with passive income through intelligent investments. I had envisioned buying operational assets that generated cash which would be used to buy more assets and support my chosen lifestyle. Before diving into the progress here, my prior position in the corporate world was Chief Product Officer for a fair sized publicly traded company, of which I ran an organization about 400+ people strong. My thinking was that if I could find the right assets to purchase, my experience and my network could help me grow those assets.

I began looking at both software companies and other types of businesses like self serve laundromats, pay day loan businesses, rentals (Air B&B), etc. On the software side, I entered diligence for a handful of companies only to discover that a) WTF are people thinking with respect to the valuations they place on their companies and b) How are business owners so distant from the performance of their own companies? No one does a better job then my prior boss in looking at a P&L and finding the areas of a business that are in peril. Bottom line may say green, but there can be all kinds of red flags regardless. Working to prepare for quarterly board reports certainly came in handy for the work to be done here. I didn’t close on? a single software business in the 1 year, but have probably looked through 50-75 P&L’s of small software companies. Its no wonder so many fail!

On the more Brick and Mortar type business, I submitted 4 offers to purchase businesses and 3 of the 4 failed on diligence. I am in the process of closing on 1 of them and look forward to the challenge of growing in a business I know nothing about. That being said, the process here was extremely frustrating. People move slowly and no one seems to care about details. Coming from a world where details were everything and speed was your advantage, the last year of working through acquiring different types of businesses has been soul crushing. The lessons learned here, were ones I already knew. The smaller the M&A consultants that I worked with, the slower they were. This is not a statement of cause and effect but one that is most definitely coincidental. If you can move quickly, and if you are prepared, you can win. You won’t always win, but it certainly gives you an advantage. There were M&A consultants that I worked with who were representing businesses who just weren’t ready for meetings and were unable to answer the most basic questions. I said on more than one occasion to them not to meet with me if you aren’t prepared.

The most meaningful work I had during the year was building on a start up in the AI space. I joined late to the company as a ‘founder’, but had been involved with it since inception and in fact was a pilot customer when first launched. The software itself was something that I really believed helped solve tangible problems for product owners, GTM teams and C Suite members. The software aimed to triangulate customer feedback specific to product. In a course of several months we learned what pain points we could talk about that would lead to meetings, what demos would lead to sales opportunities and what price points we need for our own GTM strategy. Unfortunately what we learned was that we needed a much longer runway than we had for lift off and we wouldn’t have made it with the runway we did have. We decided to wind down and look for other opportunities.

Those other opportunities are what I currently invest my time in under the banner of LeapMotiv (https://www.leapmotiv.com), a consulting agency to help companies explore adjacent markets and innovation pathways to help drive more revenue. If you’ve made it this far, I’m hoping that some of you take the time to connect with me on where I believe I can help. My craft as an executive was and is my ability to break down problems and solve them through quick decision making and having properly deconstructed what I try to solve for. I’ve been especially effective in a CPO role where the craft is pointing the ship in the right direction in line with internal stakeholder needs and customer/market needs. Those two worlds don’t necessarily see eye to eye because customers look at current needs but a company has to look ahead and predict where needs may be going. As a fractional CPO, or mentor to CPO/CTO resources in place, I would love to work on helping teams strategically organize themselves to handle the balance between present needs and future needs, understand adjacent market opportunities, increase velocity of output and be able to baseline productivity. I’m especially interested to understand where AI is helping teams and how that help is being measured.

In reflecting on my year, I can say I’m honestly not where I want to be, not necessarily focused where I want to focus but I have made strides in very specific areas. I’ve also become really adept at shortening the amount of time it takes me to find red flags, identify what is worth spending time on and having dipped my toe into ‘retirement’ know for certain its not time. While I know I do not want a traditional role, I do want to work on meaningful projects and am ready to discuss what that may be. Ideally, there’s something to our work at LeapMotiv that intrigues you, and/or looking for help from a fractional CPO type because this is where I offer the most value. Also, as a last point, being involved in a diligence process for acquisition and doing it for yourself are two very different things. Owning risk, putting your own blood sweat and tears on the line for yourself is worlds apart than doing it either with someone else’s money or under someone else’s banner. I’ve said it before and I’ll say it now, waking up in the middle of the night wondering how you're going to make payroll changes you.