Latest / Solopreneur Sessions with Fexingo: One-Person Businesses, Freelancing, and Independent Work / How a Solopreneur Used LinkedIn DMs to Land a Six-Figure Retainer
Transcript
- Lucas: So there's this story that keeps rattling around in my head. A former marketing manager named Sarah Mitchell — she launched a brand strategy consultancy from her living room in early 2024. No website, no portfolio, no paid ads. And within two years, she was pulling in a hundred and eighty thousand dollars in annual recurring revenue — almost entirely from LinkedIn DMs. Luna: A hundred and eighty thousand? Just from direct messages on LinkedIn? That's wild. No website at all? Lucas: No website. She had a bare-bones profile, a few posts, but the magic was in the DMs. She landed her first three retainer clients in five weeks — all founders of B2B SaaS companies — using a four-step outreach sequence that felt less like a pitch and more like a conversation. Luna: I want to hear the exact sequence. But first — and I'm going to tie this to the topic — one thing that makes these conversations possible is that the show stays ad-free, and that's because of listeners who chip in. If these episodes have helped you think differently about your own solopreneur journey, supporting us at buy me a coffee dot com slash fexingo is a simple way to keep the lights on. Lucas: Yeah, it genuinely does make a difference. And it lets us keep drilling into these detailed, tactical stories without any commercial breaks. So — back to Sarah's sequence. Step one is what she calls the observation-based opener. Luna: I'm guessing that's not 'Hey, I saw your profile, let's connect.' Lucas: Exactly. She'd spend ten minutes reading a prospect's recent posts, their comments, their company's blog. Then she'd send a two-sentence DM referencing something specific — 'Loved your take on product-led growth in the latest post. The point about user onboarding frequency really hit home.' That's it. No ask, no link, no pitch. Luna: So she's opening with genuine curiosity. That already puts her in the top one percent of LinkedIn DMs. Lucas: Right. The second step — and this is where most people drop the ball — she follows up two to three days later with a value-drop. Not a quote or a statistic. She shares a one-paragraph insight tied to their business. For example, a prospect in fintech got this line: 'I noticed your competitor just launched a round of referrals tied to banking data. I've seen that trigger a 20 percent uptick in retention in similar verticals. Happy to share a case study if it's useful.' Luna: That is a lot more useful than 'just checking in.' She's giving them a reason to reply. Did she get responses? Lucas: She told me about sixty percent of prospects replied to that second message. And from there, step three is the case-study callback. She'd reference a similar challenge she solved for a past client — but framed generically so it doesn't feel like a testimonial drop. Something like 'One of my clients in a similar spot saw their brand awareness scores double after a positioning refresh. I'm not sure it's right for you, but it might be worth a fifteen-minute chat to compare notes.' Luna: Soft, specific, low pressure. And step four is the ask — but only after she's had a reply, right? Lucas: Exactly. Step four is the soft ask. She proposes a specific next step: a thirty-minute call to explore a project. Not 'let's hop on a call sometime.' She says something like 'Would next Tuesday afternoon work for a thirty-minute call to see if a positioning refresh could move the needle for Q3?' That specificity alone probably doubled her conversion rate. Luna: I love this. But I have to ask — does this scale? At some point, you can't spend ten minutes researching each prospect if you're sending fifty DMs a week. Lucas: That's the tension. Sarah automated the research part using a combination of LinkedIn's saved searches and a simple CRM where she logs prospect signals. She built a library of common observation templates — common triggers she sees across industries. So the opener becomes a fill-in-the-blank. But the value-drop is never templated. She writes each one from scratch. That's the non-negotiable. Luna: So the automation happens on the front end — the prospecting — but the actual conversation stays human. That feels like a sustainable balance. Lucas: It is. And it's a big reason why DMs can outperform cold email for solopreneurs. Cold email has become a noise channel — everyone's inbox is flooded. LinkedIn DMs still feel like a one-to-one channel, especially when they're thoughtful. Sarah's open rate on her first message was around eighty percent, compared to maybe thirty percent for a cold email. Luna: Eighty percent is insane. But I wonder — does this only work for B2B services? Could a product-based solopreneur use the same approach? Lucas: I think it's harder for products because the purchase decision is quicker and often lower-ticket. But for high-ticket services — consulting, coaching, design, development — it's almost ideal. The DM allows for a nuanced, value-first conversation that builds trust before you ever ask for money. Luna: One thing that strikes me is how much upfront effort she put in before she had any results. Five weeks with no replies from some prospects, and she just kept going. That's a mental game as much as a strategy game. Lucas: Totally. And she told me she tracked everything — response rates, conversion rates, time spent per prospect. She found that her sweet spot was targeting companies between ten and fifty employees. Too small and they can't afford her. Too large and the decision-maker is buried. She optimized that over time. Luna: That's the kind of data most solopreneurs never collect. They just blast out messages and hope. She's running it like a mini sales lab. Lucas: Exactly. And the result is that she now has a waitlist for her services. She actually raised her retainer rates twice in the last year — from three thousand a month to five, and then to six. And she still gets inbound from the DMs she sent months ago. Luna: So the sequence itself becomes a kind of asset. Those conversations keep paying dividends long after the initial message. Lucas: Right. And it raises an interesting question for anyone listening: what would it look like to replace the 'spray and pray' approach with a deliberate, small-batch outreach engine? Even if you only reach out to five prospects a week — if you follow a sequence like Sarah's, the compound effect over six months is enormous. Luna: I think the biggest takeaway for me is that the barrier to entry is just time and thoughtfulness. You don't need a big following or a fancy website. You just need to care enough to write a genuinely useful message. Lucas: That's the thesis of the whole show, really. Solopreneurship isn't about outspending the competition — it's about out-caring them. Sarah's story is a perfect example. A living room, a laptop, and a four-step DM sequence that generated nearly two hundred grand a year. Luna: And she's not alone. I've seen similar patterns with freelancers in design, copywriting, even accounting. The details change, but the principle is consistent: lead with observation, add value, then ask specifically. Lucas: If you try this — and I hope some of you do — the one thing Sarah emphasized is to track your numbers from day one. Know your response rate, your conversion rate, your average time per prospect. That data tells you where to double down and where to cut. Luna: Alright, I'm going to start tracking my own outreach this week. I've been lazy about it. So thanks, Sarah, wherever you are. Lucas: And if you have a solopreneur story you want us to dig into, drop us a DM — maybe not with the four-step sequence, but we'll read it.