Welcome to Issue 19 of A Good Reputation, a newsletter about a good brand move that helped grow a small business. (Did someone send you? Subscribe here.)

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Hello Reader,

I’m gonna go out on a limb here and make a bold claim: Starting (and quickly scaling) your own business isn’t that hard.

Maybe—just maybe—you’re not ready to do it.
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I stayed up way past my bedtime last night getting sucked into my shiny new LinkedIn video feed and noticed something my 9-year-old would say is totally “suss.” (Did I spell that right?)

The majority of people posing as marketing experts couldn’t possibly have more than a couple of years of experience in the workforce—if any at all. Chances are they’re still living in their parent’s basement.

I mean, I can’t see a single wrinkle on their forehead—much less a line of actual proof on their resumes.
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Yet, here they are, all over my social feed, trying to teach me about building a sustainable brand, growing an audience, and/or building a successful business.
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I’m not trying to pull a reverse agism move here and say that all these annoyingly overconfident 20-somethings (we’ve all been there) don’t have something to teach. I believe there are plenty of things we can learn from every generation—my 6 and 9-year-old kids included.
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All I’m saying is that there’s something to be said for starting your business after you’ve gained some real expertise working for someone else.

Why?

Because it makes the whole process much easier.
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Not only do you have a more robust network to tap, you have real insights from making lots of mistakes on someone else’s dime.
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I know that if I had tried to start my business earlier—this business—I would’ve messed it up. But since I started it after over a decade of learning how to write for the internet, I was able to replace my full-time salary in under a year.
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And today’s story is about a friend and fellow freelancer who did the same.
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After 25 years in corporate, Lee Densmer decided to launch a content marketing consulting business in her 50’s. Within 6 months of going solo, she not only replaced her full-time tech salary—she exceeded it.
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And even though she dealt with self-doubt and imposter syndrome, she had the confidence that a lot of experience gives you to pull it off. In fact, she made it look easy.

Her approach? Simple, swift, and straightforward with a killer LinkedIn strategy to get new clients on the phone and into high-ticket retainers.

Let's dive in.

A Good Story

When they had a little extra cash, Lee’s parents were the type to choose traveling around the world instead of fixing the roof.

So, when Lee’s dad got the opportunity to skip the Vietnam War and go work in a milk factory in Arequipa, Peru, he took it. Lee was born there shortly after and picked up her first words in Spanish.

Eventually, her family moved back to the States, and Lee brought her worldly wanderlust—along with a love of learning Spanish—with her.

When looking for her first job, a role or industry that allowed Lee to use her Spanish and travel was high on the list. After a short stint as a project manager for technical documentation at Hewlett Packard (read: product manuals), Lee got into the world of content for a global translation company.

For the remainder of her career, Lee did just that. While she jumped around from one large global corporation to the next, she stayed within the translation and localization industry—often working for her previous employer’s competition.

Lee planned to stay on that corporate course until retirement. But then, the thing most corporate employees fear happened:

She got laid off.

A merger wiped out her entire department and Lee was left scrambling for a new role in a new company. She sent out over 200 applications and, from that, landed 20 interviews.

Out of those grueling 20 interviews, (including a couple of IQ and personality tests) she got a decent offer and took it.

The process, as she describes it, was soul-crushing. And the new role quickly proved to be underwhelming, with a toxic CMO who had unworkable demands. But at that point, she was just grateful to have landed in a new role with benefits and an IT salary.

And then (because corporate is the worst) it happened once again: After just over a year on the job, Lee’s role got cut.

So, she was faced with a choice: Go through that soul-crushing goat rodeo again or start her own thing.

After a full career in corporate, Lee doubted that she could start something new in her 50s. Not only did she face the usual self-doubt and imposter syndrome demons we all deal with, she also feared ageism and sexism.

But, with her strong network and content marketing expertise in a (very) niche industry, she had just enough confidence that she could pull her own thing off.

Her husband, worried about the loss of income and putting a kid through college, had some nerves about the whole thing. (Men!) As a family, they decided to give Lee one year to replace her lost salary and make the business work.

Determined to prove to her son, her husband, and herself that she could succeed at her own thing after only ever working for other people, Lee got to work.

A Good Approach

Using a business plan template she found online, it took Lee three days to outline her offers, buy a domain, establish an LLC, and create a corporate LinkedIn page. And—proving you don’t need anything fancy—she even made herself a legit-looking logo.

Maybe because she’s an actual adult (or maybe because she had no time to waste), Lee also bought all the business books, listened to the best entrepreneur podcasts, and joined a couple of business coaching communities.

She realized that running a sustainable business is a skill that needs to be learned, and she was determined to learn it quickly. (This is a not-so-subtle nod to all of us entrepreneurs who try to wing it and then wonder why it’s taking us so long to figure it out.)

To land her first client, Lee went back to her network and reached out to a woman who offered her freelance work when she was still in-house. As luck would have it, the connection still needed the help. With that, Lee was in business.

But, Lee couldn’t afford to rely on her existing smallish network alone to find new clients. She knew that in addition to one offer (content marketing strategy and execution) for one industry, she needed one channel to build her reputation and reach prospects.

Naturally, she turned to LinkedIn.

As a content marketer, Lee already had tons of ideas to share her expertise online. Posting was the easy part.

Every day, she wrote a valuable post, sent connection requests, and engaged with her audience. While she grew fast, she knew that wouldn’t be enough.

So, she went hard on personalized outreach to new buyers in her niche, where she quickly realized finding the right person to pitch is half the battle.

And guess what? It worked.

Within six months, Lee booked eight high-ticket retainer clients and blew past her goal of replacing her previous full-time salary within her first year.

Using keywords and filters to find the right people at the right companies in her specific niche, she’d search for roles just below or above where she’d fit into the marketing department. If the company had a senior content marketer, that was her signal to move on. If they had a writer and then a CMO, she could pretty safely assume they needed strategy help.

In short: She focused on companies and departments where her services could fill a gap. (THIS!)

Next (and most importantly) came learning how to engage those people and get them interested in talking with her.

Instead of connecting and quickly dropping an offer on a prospect, Lee took a more personalized, curious, and helpful approach.

First, she’d send a connection request with a message aimed at kicking off a conversation.

Next, she’d review a company’s online presence—whether their website, social media, or LinkedIn profile—and share a compliment (where possible) and then offer specific feedback on how they could improve their content marketing.

But get this: Instead of just sending her findings in a message, she’d record and send a short Loom video.

Brilliant? I think so.

By sharing insights tailored to her specific prospect, she was able to showcase her expertise and start the conversation with a ton of value.

And by doing it in video form, she was able to show a little bit of her personality and energy. (Side note: Did you know that Loom notifies you when your video gets played and passed around? Can’t do that with a written message.)

She didn’t give up there. If a prospect wasn’t biting on LinkedIn, she switched platforms, using a tool to find their email and follow up outside the noise of social media.

For Lee, it was all about finding the right touchpoint. (And for me, a good reminder that sometimes all it takes is a little persistence.)

Only a year and a half into running her new business, Lee is killing it by all measures. She has a steady flow of high-ticket clients and a library of LinkedIn posts to keep her active on the platform through November.

With her son now successfully off to college, she even has some extra room to experiment. After a year and half, only now is she considering creating new offers or (maybe) even building a course.

A Good Lesson

One lesson Lee learned the hard way is that not all coaches are created equal—and she spent a lot of money on one only to figure out it wasn’t the best fit.

While Lee admits she believes in the power of coaching for new business owners, she found way more value in teaching herself through business books and joining communities of entrepreneurs.

The best ones, she says, are run by generous coaches who aren’t just there to pad their own bank accounts.

A Good Takeaway

Lee’s approach to replacing (and exceeding) her full-time salary and building a thriving business in under a year came down to one thing:

Simplifying.

She stuck to one industry she knew with one core service offering and focused on one channel for her marketing and outreach.

For a lot of us with shiny object syndrome, this is a big one—and I’m probably the most guilty of us all.

I’m always thinking about the next thing I can experiment with or offer I can build to diversify my income streams. And until a few months ago, I was active on multiple marketing channels.

But, unlike Lee, I have a little more time and space to experiment. I don’t have the pressure of giving myself only a year to make it work or pack it up.

If your back is against the wall, maybe thinking about building that course or launching that community comes later. It's about doing one thing in the right order in a way that works for you.

As for how Lee specifically leveraged LinkedIn to build her reputation and land dozens of high-ticket contracting retainers in under a year, here’s what I took away:

1. Start by identifying and targeting the right decision-makers. For Lee, that meant people in positions just below or above the role she’d fill in marketing departments. The key is to look for companies in the industry you already know and avoid targeting those with people in roles who might see you as redundant.
2. Take a curiosity-based messaging approach (Translation: Don’t pitch—start conversations). In connection with requests and messages, lead with curiosity and offer something valuable rather than making a blunt sales pitch. Keep messages concise and relevant, focusing on the potential client’s needs, not your services.
3. Give personalized advice, feedback, or value (In video!): Examine a potential client’s online presence (website, LinkedIn, social media) and offer them tailored insights that clearly demonstrate how you can help. And if you really want to stand out, take a page from Lee’s playbook and deliver it in a video or voice message.
4. Focus on outreach as much as posting: Lee agrees with most experts that you don’t need to post on LinkedIn more than three to four times a week to stay visible. She does it anyway because it comes easy to her. But if you want to use the platform to make more lucrative connections with potential leads, Lee suggests focusing more on outreach than sharing your expertise through content.
5. Track engagement beyond the platform: If a lead isn’t responding to LinkedIn messages, consider following up through email. This gives you another access point to keep up the conversation.

Meaty strategy, no?

The funny thing is that Lee and I have taken a completely different approach to LinkedIn. I've grown by experimenting and exploring. The process has shaped my thinking and my offers—not the other way around, like Lee.

But, again, we have different goals and pressures.

Now that one of my offers includes high-ticket brand story workshops for start-up teams, I might try this direct messaging approach. (I'll let you know how it goes.)

I have no doubt that if I stuck to one industry with one message and one offer, I'd book more of those workshops, faster. But, I'd probably be bored.

My point, as always, is to learn what works for someone else and apply what works for you.

A Few Good Resources

1. Lee read a ton of business books before getting started. Her favorites? Rework, Two Weeks Notice, and Rise of the Youpreneur.
2. Smart Gets Paid is an excellent podcast for female solopreneurs.
3. While I love Thomas Strider, I haven't joined his community. (Lee highly recommends it.)

Hope you have a good one,
Renee