Winter 2008. The bottom fell out.

Startups that raised were quiet. Preserving cash. Not adding headcount.

I was in finance, trying to get out.

I thought I needed an MBA. But what I really needed was exposure.

I talked to VCs. Some were helpful. Most gave the same advice: do two years of consulting, consider getting an MBA, and then see if something opens up.

I didn't want to wait, and I didn't want to take on more debt.

I wasn't an engineer. I wasn't a developer. I was a geek, but not technical enough to ship code. Sales felt like the only way in.

So that became the plan. Get a sales job. Break into a startup. Make it count.

Searching for a Way In

Every night after work, I scanned VC portfolio pages and Craigslist.

That's where I found LocaModa, a place-based advertising platform. I clicked through, saw the team, and found Steve King, the second sales hire at Facebook when they were still in Boston.

At the same time, I was casting a wide net on Craigslist.

Yes, Craigslist.

Back then, it wasn't just free couches and missed connections. It's where founders posted listings like:

"Social Media/Marketing/BizDev at TechStars-funded startup (Cambridge, MA)"

Real-life job posting on Craigslist, circa 2009.

No job title. No salary. Just vibes. I replied to every one of them.

I was young, hungry, and had nothing to lose. So I chased people.

Most of the Craigslist replies got me nowhere. But Steve was different. He always replied. Not with an offer, but with time. So I kept showing up in his inbox.

Persistence Over Permission

I was in touch with Steve off and on for nearly a year. We finally met in February 2009.

He wasn't hiring junior salespeople. Said it was too early. But he always replied.

Cold emails. Quick follow-ups. Always there. For months, nothing opened up.

Then, in September 2009, I sent this:

"To be candid, I want to join your team and become a sales/marketing intern. I'm fully employed but still have the desire to get on the ground floor and help build a winning product. I have no problem putting in endless hours."

His reply landed in my inbox the next morning:

"You want to intern? Make cold calls? Dial for dollars? Log hours in Salesforce? For free? While working full time? How will this work?"

I laid it out:

"I used to work 80-hour weeks as a headhunter. I was gunning for investment banking. 100-hour weeks didn't scare me. State Street caps me at 36.25 hours. I get out at 4, I'm at Central by 4:30, and I can make calls until the West Coast signs off. I'll work weekends. I'll make calls at lunch. I'll do whatever it takes."

I told him I wanted to be the little sales bitch that could. And that was enough.

No Playbook, Just Reps

Coming out of the financial crisis, banks cut everything. Bonuses, overtime, all of it. At State Street, I wasn't allowed to work through lunch. They made me take it.

So I walked to Panera, fired up my laptop, and sent cold emails for LocaModa.

After work, I took the T to Cambridge and arrived at the office just as most people were packing up. I'd stay until 11 pm most nights, sometimes later. I sent emails from my couch. I worked weekends.

There wasn't any structure. I created momentum.

Some companies, like Ford, were still on Lotus Notes. My emails kept bouncing. Then I remembered from a college internship. Lotus Notes capped email names at eight characters. I chopped off the last name, tried again, and it worked.

No Apollo. No lookup tool. AdDatabase helped sometimes, but it wasn't always right.

Most replies were no. A few were "f*** off." One was yes.

One Yes Changed Everything

That yes led to a global Vans campaign. Seven languages. Times Square billboard. Biggest deal the company had closed at the time.

A few weeks later, the full-time offer came through. I gave notice at State Street. Started unpaid in September. Full-time by December.

The email confirming my full-time offer. About 2.5 months after starting as an unpaid intern.

One Yes Is Enough

I heard a lot of no's. From people I wanted to work for. From people I was trying to sell. But I kept showing up.

Most people wait for the job to open. For it to show up on LinkedIn, for someone to post the role, for perfect timing.

I didn't wait. I showed up before I was invited.

I didn't know the industry. Didn't know how to sell media. But I knew how to follow up, stay hungry, and make myself useful.

Those cold emails changed my career. The reps I got after them changed everything else.

I didn't stop chasing after that one yes. Still haven't.

Greg