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Front Page › Markets & Main Street › Small Business

Dinner Deals

they wanted someone older

Vintage desk with a rotary telephone and handwritten notes illustrating early stage cash flow struggles.
A workspace set up for cold calling, reflecting the reality of early client outreach and uncertain income.

I was twenty-three, three months married, living in a country I had moved to as an adult, and I had no salary at all. This is what one February looked like from the inside.

On the 6th of February I rebuilt my resume from scratch. It was the third time in three months. What interests me now is not the resume — it's the two lies I put at the top of it.

The first was the address. Two weeks earlier the same document had carried the name of the small town where I'd spent all of January trying to start a sports league. The new version carried a different town entirely. We had moved. There is no email anywhere in my archive about that move — no lease, no movers, no congratulations. The only record that it happened is an address line quietly changing between one job application and the next.

The second was the header. I gave myself the title "Student at" a college I had not enrolled in. Under Education I wrote the degree and the years. I hadn't started. I wouldn't start for months. But I had decided, and at twenty-three I decided that deciding was close enough to write down.

Then I spent the rest of that Monday firing.

3:22pm, to a music ad: "Hi I'm very interested. I studied music in [music school] and currnetly I am working to produce a show." 3:30pm, to a rabbi, asking to join a morning learning program. 3:43pm, to a startup: "I think you would find that I am very orgnised, efficient and driven, and I can really take your startup to another level." 9:15pm, a sales executive job. 9:45pm, a medical billing job.

The typos are all still there. Orgnised. Managorial. Alot. I wasn't proofreading. I was covering ground.

The next day I opened a seller account on a freelance marketplace. Welcome, they wrote. We're thrilled you've joined our seller community. I never listed a single service.

THE PHONE CALL I WASN'T OLD ENOUGH TO MAKE

There was a man who ran a small consulting outfit and farmed cold-calling campaigns out to people like me. On the 7th he wrote: another client wants to hear you out. What time can you take the call tomorrow?

My replies that night are painfully eager. "I will be available at around 8 for sure just that good?" Then, at 11:44pm, having actually looked at my week: "OK so it looks like I can probably do around 12 ish let me know if that's good."

The next morning he sent me the entire job in one block. A phone number in a country I'd never called. A shared login for cheap international calls, username and password in plain text. The brief: get people to attend an investors' conference on the other side of the world. And the instruction — "It's B2B so tell him you know how to tackle B2B and to get past the gatekeepers to the decision makers to convince them."

Tell him you know. At 11:23am I replied, honestly, to precisely the wrong person: "Hey I got it, never done b2b just looking it up."

To his enormous credit, he taught me instead of dropping me:

"It's the same as b2c just that you're usually calling a business. The best way to tackle these calls is usually tried to understand who is it you need to speak with, look for his name in the company site and try to ask specifically for him. Usually you have a gatekeeper you need to get passed and once you do it's exactly the same. You need to be able to intrigue the person on the other side of the call to have him interested in your pitch."

That is still, functionally, the whole of B2B sales. I got it free, at twenty-three, in an email at 11:31 in the morning.

I made the call. At 12:46pm I reported back:

"Hey, he said he was looking for someone older to do the calls. Apparently the guys he's selling to don't take kids seriously. So he wants to know if you have anyone older to do the sales."

I typed that with no visible reaction. No argument. No "give me another shot." I relayed it like a message boy and moved to the next thing.

Six days later the same man came back with a real, paid campaign — five hours a day, going to eight. I turned it down: "I definitely cannot do full time, the best I can do is 25 hours a week."

I was applying to everything, and refusing the one thing actually offered, because I was holding my calendar open for something else.

THE SOMETHING ELSE

The something else was a coaching job with the national federation of the sport I'd played since I was a teenager. They asked to meet — "time is important," they wrote. We met. Four days later I sent the one email from that whole winter where I sound like an adult rather than a kid grabbing at something:

"It was great meeting you guys. I spoke it over with my wife and we decided that I can fully commit to work with the team. I think it's a good idea as you said to start off as mostly a management position and see how it goes from there."

The answer came on a Sunday evening. He tried to phone first so I wouldn't read it cold — I'll say that for him. Then: they had chosen other candidates for head coach and assistant coach of the national team.

There is no reply from me in the record. Not that night, not that week. Both times that month that someone I respected told me no, I said nothing at all.

WHAT THE MONTH ACTUALLY PAID

A retailer wrote that they had no position suitable to my skills and experience. An agency abroad asked where I was resident and I answered with a residency I no longer really had.

A mother wrote me four words with no greeting: "Do you have a girls group. How many years experience do you have." I answered: "Yes I do have a girls group that I'm starting right now." It did not exist. Two hours later she wrote that her daughter had no free time. Maybe next year. I wrote: "No problem good luck!"

The morning learning program's free trial ended and they asked if I wanted to enroll properly. I never answered — I couldn't pay, and I couldn't say so either. But when the rabbi himself asked whether I still had the written material, I answered inside the minute and asked for a fresh set. I kept taking the sheets.

Then, on the 2nd of March, a payment notification arrived: a mother settling up for her son's last two guitar lessons. Fifty dollars, less the fee. Just under forty-eight net.

That was the month's entire income. Not the national team. Not the consulting outfit. Not the sales job, the billing job, or the agency abroad. A parent six thousand miles away, paying for two lessons.

WHAT I'D TELL THAT KID

The free education is real. The best sales training I ever got arrived unasked, from a man who had every reason to just drop me. Take the lesson even when you don't get the job.

Don't hold the calendar open for the prestigious maybe. I turned down paid work to stay available for a role I didn't get.

When someone says the problem is your age, that's information about them, not a verdict on you. Answer it anyway. Silence isn't dignity; it's just silence.

Writing down the thing you've decided isn't quite lying. But you have to go and make it true, fast, or it curdles.

Count what actually paid. The month I chased five careers, the money came from the least glamorous thing I did — and from a customer who already knew me. It nearly always does.

questions merchants actually ask

How do you get past gatekeepers in B2B sales when you have no experience?

Find the exact name of the decision-maker on the company website or directory before dialing, and ask for them specifically by name. Gatekeepers expect cold callers to be vague; asking for a specific individual gets you treated like an expected call. Once you get transferred, focus entirely on intriguing the decision-maker with a short, relevant pitch rather than trying to explain your entire service to the front desk.

Should a struggling business owner turn down guaranteed work for bigger opportunities?

Holding your calendar open for a prestigious offer that has not been finalized is one of the quickest ways to run out of money. When cash flow is at or near zero, bankable hourly income must take priority over speculative deals. Take the paid hours that are immediately available, then negotiate your time commitments if the higher-value opportunity actually materializes.

Where does revenue usually come from during a severe business cash flow drought?

Immediate income almost always comes from your existing contacts and unglamorous past services rather than brand-new cold pitches. While cold outreach is necessary for pipeline growth, invoices paid during critical shortfalls typically come from past clients who already trust you. Focus immediate collections on outstanding balances and repeat business before relying on unvetted prospects.

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MCAFax was built to do the thing you can't do from inside the room: make the phone stop. Check any broker against our member-built database, send cease & desist letters from your own Gmail, and build the paper trail. Some laws, like the TCPA, put statutory damages on illegal calls — whether they apply to your calls depends on your situation, and business lines get less protection than home ones. It's free, and we're not a law firm.

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