I’ve been doing cold outreach via email and LinkedIn but still can’t land my first meeting. What strategies do you suggest for improving my outreach and what advice do you have for bootstrapping solo founders?
When a campaign isn’t working, pretend you are a prospect on LinkedIn (or the platform you’re using) and walk through every element you control: profile picture, title, how recent your post is, and the actual message text. Optimize each piece—use a clear, professional photo that shows you as young, motivated, ambitious, and intelligent; craft a title that conveys credibility; consider posting timing (you may prefer to engage bottom‑to‑top); keep your message concise (around four lines before it cuts off) and experiment with capitals and emojis to grab attention. Treat the video or content you’re responding to as another input you can adjust. By enumerating all possible inputs and independently optimizing each, you compound small improvements (5 % here, 5 % there) into a large advantage. Apply the same logic on Upwork: use bright profile pictures, keep profiles to six lines or fewer because Upwork truncates after that, and write a tight, high‑quality CV (about 150 characters) with a strong, face‑focused image. These micro‑optimizations add up to an unstoppable edge in outreach.
If you haven’t considered it yet, let me walk you through it. LinkedIn is just one of many platforms; you can copy the same approach to virtually any other social media site. For example, on X you can skip the connect request, which would double your outreach, and on TikTok you could triple it. Facebook, Instagram, and other Meta platforms work similarly. If you’re running out of outreach capacity but still have time, simply expand to other platforms using the same method, making minor platform‑specific tweaks. On Instagram, a common hurdle is getting funneled into message requests; a strong opener like an open‑ended rhetorical question—e.g., 'Hey, do you do one‑on‑ones?'—can move prospects into your chat box. The core strategy stays the same; only the tactics change. Beyond social media, think about email, phone calls, or even walking up to a local business. With so many channels, a rational person could easily fill an 8‑hour day just reaching out. So, get after it—put the pedal to the metal. If you finish your outreach in the first hour, you could easily 7× your current volume, and with more reps you’ll gain efficiency and effectiveness.
I'm not a big Twitter guy—I only have about 4,000 followers, which is very few. I'm not running any successful LinkedIn campaigns either; I have around 5,900 followers and I'm not very good at it. YouTube is where I'm strong, and video content works well for me. I get your point about social proof from profiles when DMing, but honestly, I don't have many tips beyond the basics: pick one thing, get really good at it, and be consistent. I usually recommend a daily cadence over a long period.
LinkedIn has been overwhelmed with AI slop — all posts are essentially AI written, and human beings have relegated themselves to being a Claude or Codex wrapper. So do not be a Claude or Codex wrapper. Write your own post. Weave things about your own life in there. Add photos that you took before Claude and Codex were even a thing — things that won't trip up a SynthID. Add pictures of you when you were a kid fishing with your mom, aunt, and great uncle. Use that as a post to talk about resilience, whatever the hell. The point I'm making is weave in more personal story. It'll help you stay relevant and also be a lot more genuine.
I treat a LinkedIn profile just like an Upwork profile — it's your own personal website, and there are a bunch of levers you can optimize like doing CRO on a landing page. Fill everything out, that's the lowest-hanging fruit: cover photo (something well-designed, even just from Canva, so it looks like you put in effort), profile picture (face clearly visible, I crop the background to white, add a little shadow, and smile at the camera), headline (a specific pitch — mine leads with being the founder of Maker School), location (I keep mine listed as San Francisco even though I'm in Calgary, just to pattern-match with people who have money), profile language set to English, a clean public profile URL, the About section, top skills, and the Featured section (that's basically the LinkedIn equivalent of an Upwork portfolio). For experience, associate yourself with something recognizable if you can — I don't technically have a company called Maker School so I've affiliated myself with 'school' to get the perceived association with a big logo people know. Then fill out every remaining field: licenses, skills, recommendations (like reviews), honors and awards, languages, interests, causes. For activity, don't make it the be-all-end-all — I'd post about once a week, but make it high-quality and specific to AI and automation, aiming for some engagement. As long as you're consistently active at some baseline level, you're probably fine.