“I feel so out of my depth”

“I’m not very good at this. I feel so out of my depth.” Me, yesterday afternoon, struggling to sketch out our business plans in a slide.

“I think this is where you really shine, D!” Teresa, reassuring me (for about the hundredth time) that I am actually quite good at this weird unknown jungle.

I’m in the process of putting together an investor deck for Outlaw Soaps, our happy little soap company (which is taking over the world, by the way), and this is all new to me on so many levels. From the actual budgeting process itself, to the articulation of our strategy, to the sexy graphics required for such presentations, I’m struggling to get the deck together in a compelling way.

Russ and I started Outlaw Soaps in 2013, and since its inception, we have stayed fairly faithful to the business plan I sketched out in my little silver notebook. The products have changed, and we shifted our business strategy a little to capitalize on shifting markets and our improved understanding of the industry, but the concept and plan was a good one.

According to that plan, 2017 was when we wrapped up our product development (it leaked a little into early 2018), 2018 was the year we worked out all the kinks in our product line and  created a business foundation to grow on… and 2019 is when we get an investor.

When we started the business, I didn’t know anything about corporate structures or investors.

Before Outlaw, I had been a cubicle worker at the Oprah Winfrey Network, putting together product specifications for the developer team to execute on the website. Aside from glimpses into project budgets and ad insertions, the business side of the Oprahverse was invisible to me. I collected a bi-weekly paycheck. For my own entertainment, I’d periodically calculate the “return on investment” (ROI) of my employment to Oprah, adding up the ad projects I worked on and measuring that against my paycheck. As long as I cost 1/5 as much as I was making, I was satisfied.

But that was for “fun.” It was very different from submitting a plan for new hires and additional marketing expenses. All my projects were responses to advertiser or editorial team requests, translating vague hand-waving into hard plans… and now I’m both the vague hand-waver and the plan generator, plus the accounting department, the marketing department, and a lot of other random stuff.

A few months ago, in preparation for getting an investor (who would want to be on a board), I assembled a board of directors – trusted advisors I had worked with on other projects or at other jobs.

I had no idea how to assemble a board, but I knew that just like we defined our customers as the kind of people we’d want to go camping with, our board would be people we could be ourselves around, vulnerability and nonprofessionalism included.

I wanted to get everyone together before we brought on an investor, so we could establish a rapport among ourselves and come up with an articulate business strategy. I wanted the investor to come to an existing foundation so we didn’t have to scramble around getting ourselves introduced, etc. It seemed like the wise thing to do.

And I did assemble the right team, that’s for sure.

As chaotic as it is inside my head, our board has been so great about introductions, laying the foundation for good board meetings, and bringing the kind of leadership our business needs.

On Monday, I’m going to San Jose for my third annual trip to the Quickbooks Connect Conference, which I’ve found to be very enlightening. This year, I’m going with an ear toward connecting with investors.

In a surprise serendipitous moment, I found that a startup incubator in San Francisco will be having a mixer on Wednesday morning. I bought a ticket just to see if some wisdom might rub off on me in the company of these slick, smart Silicon Valley types.

With this business, we’ve stayed focused on being our authentic selves and bringing our earnestness to everything. We’re hard workers. We’re scrappy as hell. We made mistakes early and with our own money so that when we finally went to ask other people for money, we could do it with the confidence that they’re making a good investment.

I hope we’ll find someone who can appreciate our authenticity, even if my slides are a little rugged looking.

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