While I didn’t have a ton of braggable bonafides around which to build a business, I spent some time in the marketing agency and sales trenches. 

Out of college at UC Santa Cruz, I landed in New York, and I worked in catering.  If you attended a six-figure Wall Street bar mitzvah in 2010, there’s a decent chance you snagged a knish from my tray.  The city hazed me – I lived in a railroad apartment in Bushwick, Brooklyn, I got bed bugs, and my roommate was a mechanic who shouted death threats in his sleep.   

After failing to land a bartending gig because I had zero connections or tattoos, and meandering through a couple semi-predatory internships, I landed a job as an account coordinator at a New Jersey-based social media agency. 

Social was still new and cool back then, and agencies could secure massive engagements via buzzwords alone.  I managed a facebook wall for a large consumer electronics brand, and if your headphones broke in 2011 and you complained on FB, there’s a decent chance you got to read my copy-pasted apology.  

I commuted everyday from Astoria, Queens to New Jersey via the Port Authority Bus Terminal, and every New Yorker reading this is probably groaning right now, so I started looking for something better.  

From a Craigslist ad I landed my next job as the first employee and account manager at a midtown animation studio called IdeaRocket (to this day, I respect Craigslist, and we throw it into the mix with every hiring round).

IdeaRocket is where I cut my teeth.  I worked in a hybrid role, shuffling back and forth between sales and account management.  I even got to contribute a metaphorical concept or two to the animated videos – “What if we used a lightbulb to represent an idea??”  In the early years, we worked out of one of the first WeWork buildings in midtown, and the glass office walls reverberated my incessant sales calls throughout the floor. 

At that time, I was task switching constantly between clients and prospects, all while glued to my inbox.  My sales process was like free jazz, but I thought that was ok because I didn’t want to over-plan and come off as “sales-y”.  My mindset was that if a client didn’t see the value right away, what more could I do?  In reality, I was a glorified order taker, and unless a prospect had already decided to buy from us, most deals evaporated.  

Predictably, revenues and cash suffered, and we hit a number of ‘feast and famine’ cycles.  I scrambled to win projects, we got busy, then there were no new opportunities in the pipeline, so I’d scrambled again, and so on.  We invested so much creative energy on our clients, but we rarely stopped to focus on ourselves.  We were up against the Cobbler’s Children Problem, something that our team continues to see at least five times weekly in agencies and service businesses.  

One day, our founder Will Gadea, who’s still a close friend, asked if I wanted to undergo sales training.  I was skeptical because I didn’t think traditional sales training would help me sell a complex creative services product.

But I humored Will, and of course he was right.  Coached by a tenacious entrepreneur named Mike Gansl, I stopped making as many dumb mistakes, like sending proposals out via email without a presentation call, and we started to fine tune a process.

Before I bounced between tasks, now I started to focus on sales or client service for large uninterrupted blocks of time.  My process went from jazz to science, and I started using a script, asking specific questions, preventing the usual objections, and maintaining the same process in almost every situation.  I built a pipeline, reduced emotion, and chose opportunities carefully, like a professional poker player would.  

We leaned into many sales channels like paid ads, outbound, PR, trade shows, and early morning networking groups, and I led thousands of sales calls over a few short years.  Through unrelenting trial and error, we developed an effective process for selling a ‘big ticket’ creative services offering, where the value is abstract.

By 2014, we secured 16 Fortune 500 accounts and had gone from nearly-zero to seven figure revenues.  We upgraded from WeWork to our own bright and sunny office space in Midtown Manhattan.  I helped secure a deal with Showtime and we produced the eighth season show opener for Weeds, starring Mary Louise Parker, and we were nominated for an award at SXSW.  I was making six-figures as a 25 year old, having fun, and working in a creative and upbeat environment.  

That’s when a little bird named Tim Ferris started chirping into my ear via his book The Four Hour Workweek.  Adding to that, over drinks one evening a friend told me about his success making four-figure monthly passive income from self-publishing business books, and he encouraged me to give it a shot.  The phrase “online passive income” sounded to me the way that “gold at Sutter’s Mill” must have sounded to 19th century prospectors, but I was unsure.

“I can’t publish a book!” I said.  Then he asked if I wrote papers in college, and since I wrote a forty-page thesis, it clicked that I could probably pull off this whole self-publishing thing. 

Zoom forward to that coffee shop in Saigon.  I went to work on what would become Mastering Account Management, a bite-sized handbook for those in hybrid sales/client service roles. 

Sales Schema back then was homebase for my books, including three follow-up publications, and for my sales consulting practice.  From the success of Mastering Account Management and networking connections in previous lives, I landed a few early consulting clients.  

Our clients then and now are busy owners and executives selling complex products and services.  They typically survive and build their companies on the strength of their rolodexes, but they hit a ceiling from an over-reliance on referrals and organic new business, which makes it almost impossible to grow, get acquired, or simply choose their clients instead of the other way around.  

Worse, they are often facing  ‘The Cobblers’ Children Problem’, where they dump most of their bandwidth into fulfillment and have little left to sell themselves.  

Sales Schema went from a coaching and consulting practice to offering courses and info products, and there were some early wins for clients, but we hit roadblocks. 

Regardless of what my clients needed, what they understandably wanted was a done-for-you solution.  

So I pivoted Sales Schema to what would become a fractional new business team focused on targeted outreach and appointment-setting.  I had a ton of experience prospecting, so I knew that landing appointments is a huge pain point for busy salespeople, who should spend 99% of their time building relationships and persuading, not opening doors.