#266 · how to actually use upwork as a beginner in 2026

youtube ↗Lead Generation

What BD strategy would you recommend for an AI automation business? Should I rely on cold calling and cold email, or are there other lead‑generation avenues I’m missing?

Cold calling is extremely time‑inefficient: spending an hour on the phone typically yields only 10–15 minutes of actual conversation unless you use a power dialer, and most people don’t use even basic tools like Clearbit. This means you operate at about 25% efficiency—the opposite of leverage. Instead of cold calling, devote that time to sending high‑quality cold emails and direct messages. The outcome is similar: prospects get a high‑quality interaction, you can appear on video, and you gain the ability to automate follow‑ups, cut through gatekeepers, and eliminate dial and connect times. Essentially, a well‑crafted cold email functions as a high‑quality voicemail that scales far better than phone calls.

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Related answers

youtube ↗Cold Email

What’s the best strategy to get voice‑AI clients – cold email with a free trial or a kickoff‑call offer – and which niche should I target, local contractors or something else?

I don’t have any voice‑AI campaigns running right now, but I’d start by targeting call‑intensive niches. Look for services where a quick phone call is essential – for example, local cleaners. Search Google for “cleaner [city]”, open the top five results, and call each one in order until you get a response. Focus on time‑sensitive, local services because they’re more likely to adopt a voice‑AI solution. Once you have a list, run a cold‑email campaign offering either a free trial or a kickoff call, depending on what resonates with the prospect. The key is to demonstrate how the voice agent can handle after‑hours calls or urgent bookings, saving the business time and increasing conversion rates.

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youtube ↗Cold Email

Why do you recommend cold email over cold calling?

Cold calling is inefficient: you spend only about 40% of your time on actual talking (10% dialing, 10% waiting for connection, 20% dealing with gatekeepers) and often never reach the decision maker. Cold email guarantees you’re speaking to the decision maker and lets you automate follow‑ups to stay top of inbox. I equate the effort of cold calling to sending cold Loom videos—Looms add video but the core effort is similar; you can skip the call time and send Looms directly via email for better pound‑for‑pound results. Cold calling does build a killer mindset, but for pure productivity cold email wins.

cold emailcold callingloom
youtube ↗Lead Generation

How can I get back into my AI agency journey and start making money after pausing for exams, given I only tried cold calling a few days and built some basic automations?

If you've only tried cold outreach a few times, you need to do it 100–1,000 times more to see results. When I started, I knocked on about 3,000 doors over three months with a friend and made only $7—roughly the same outcome as 5–15 cold calls that got zero replies. At the beginning, lacking experience means you need many reps to win. I wouldn’t recommend cold calling for selling automations today; instead, send custom Loom videos. They avoid synchronous timing issues and gatekeepers, letting your message sit in the prospect’s inbox, which is far more effective—likely three to four times better use of your time.

cold callingloom videooutreachreps
youtube ↗AI & Automation

Hey Nick, what are some automations, builds, and offers that can be easily sold by beginners on cold traffic? Is it strictly stuff that brings new money or clients to the company? And is there something automation related rather than say cold email?

Cold email isn't really automation; you can easily build an AI‑enabled cold‑email agency, which is a top solo‑freelancer model right now. But the simplest, highest‑leveraged system you can build for a client is a 'speedtole' system—a glorified autoresponder. You watch a mailbox for incoming mail from a filter (e.g., Facebook lead ads sending an email), then using Make.com, n8n, or cloud routines you scan the mailbox, get the trigger, and immediately reply via email. Then you send a Twilio SMS, and a team member calls the prospect. This cuts response time from minutes to under a minute, boosting pickup and conversion rates because of the perceived professionalism of your system. I’ve seen this system add over a million dollars in revenue for clients and improve existing funnels by 10‑20%, easily generating an easy $500k per year.

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