Solopreneur Stories

In this episode I speak with Michael Strachan.

Michael has served in all roles of digital agency life, starting in the weeds, overseeing cross-channel teams in multiple locations, developing strategy for companies of all sizes including several fortune 500. 

He’s since gone on to found Mediaconfidant.

The initial market opportunity Michael saw was identifying where data was inaccurate - in his agency life he saw more clients leave due to fights over what the numbers were than actual performance, so he created a tool to identify not only what the issues were but where they came from.  

When he showcased it to Google, they put MediaConfidant in their Google Startups for Cloud program at the Scale level and awarded them dev hours to build the next gen of reporting that includes forecasting, data source comparisons, anomaly detection, PII detection, hacking vulnerabilities, and real actionable insights. 

Michael is an old colleague and friend and it was great to catch up with him.

We cover other topics including:

And other topics.

Please enjoy my conversation with - Michael Strachan.

In this episode I speak with Garrett Jestice. 

Garrett is a GTM Strategy consultant and advisor for B2B startups. 

Before founding Prelude Marketing, Garrett was the Chief Marketing Officer for Eddy, where he helped build a successful go-to-market strategy that boosted revenue 3x and website traffic 10x in his first 18 months in the role. 

I reached out to Garrett to come on the show. He is someone who operates in a similar space and function as I do, and he wrote an open letter to himself on LinkedIn that covered some of his current thoughts on his own future in solopreneurship.

If things go well, there seems to be a somewhat inevitable intersection one faces with their solo operation, which includes scenarios like:

You get the idea.

Garrett was super easy to talk to. He’s a great guy with a lot of smarts, and there were moments where I felt like I was talking to the voice in my own head with how similar some of our experiences have been.

It was a ton of fun, and another conversation I got a lot of lessons and value out of.

And I think you will too.

So here it is.

Here is - Garrett Jestice.

In this episode I speak with Rachel Meltzer.

Rachel is a freelance tech writer, writing business coach, and also host of her own podcast, The Guidebook.

Rachel and I cover topics including:

And other topics.

Since filming, Rachel and I have become pals. We’re both located in New England, Rachel in Massachusetts and myself currently in Rhode Island.

We’ve been hosting meetups at some local breweries to connect with other fellow freelancers, consultants, and solopreneurs in the New England area.

It’s been a lot of fun - meeting new people, discussing what’s working and what’s not, making introductions to each other’s network, and all the good stuff to help each other learn, grow, and win out there.

So if you’re a New Englander, stay tuned for more events - we’d love to see you there.

For now, here’s my conversation with - Rachel Meltzer.

In this episode I speak with Christy McCreath.

Christy is a seasoned B2B marketing strategist with over 15 years of expertise in revenue marketing.

She specializes in Account-Based Marketing strategy and execution, and managed services for ABM tech implementations.

Christy brings efficiency and data-driven insights to drive programmatic successes for GTM teams at medium-sized tech companies.

We cover topics including:

And other topics.

Christy was great to speak with. I wanted her on the show to share her story as, to date, I had not had anyone specifically focusing on Account Based Marketing as a solopreneur.

For those unaware, doing this requires one to be a veritable one person army - which Christy is. Carrying both technical expertise in different marketing technologies and also business expertise in understanding the big picture strategy a business needs to have in place before committing to an ABM program.

She was a ton of fun to speak with and I think you’ll enjoy hearing her story.

So, here it is.

Here is - Christy McCreath.

In this episode I speak with Gargi Potdar.

Gargi is an Agency founder and Solopreneur, at GKP Consulting.

She’s a passionate and driven founder and marketing growth consultant who specializes in B2B marketing for startups and scale ups.

She’s built successful demand generation growth functions and thrives on aligning sales and marketing to work together and not against each other. 

Gargi started her solopreneur journey a little over a year and a half ago so that she could spend more time with her son and make her own schedule. 

Probably something that resonates with any fellow or aspiring solopreneurs who might be listening. If so, stay tuned for how we explore that topic.

Speaking of topics, we  cover ones including:

And other topics.

Apologies to my audience for how I sound in this episode. 

I was on the cusp of losing my voice from a cold that made me a bit froggy, so I hope it doesn’t come off as too rough on your ears.

Anyway - Gargi was a great guest. I loved her story and really appreciate her taking the time to share it with me.

And now it’s shared with all of you - so please enjoy my conversation with - Gargi Potdar.

In this episode I speak with Peter Wilken.

Peter is a Madman, Brand Man, Dad-man, Coach-man, Author and Speaker. 

He used to run ad agencies, his last corporate role being Head of BBDO Asia Pacific. He also ran agencies for Leo Burnett and Ogilvy before co-founding one of the first specialist Brand Consulting firms, The Brand Company. 

Peter continues to consult through his private company, Dolphin Brand Strategy, but increasingly spends his time coaching business owners and aspiring brand strategists and Chief Brand Officers through his online programs at The Lighthouse Brand Strategy Academy.

Peter was a great guest. We cover topics including:

And other topics.

We had a little bit of network challenges while filming. All my fault. But Peter was a total gentleman rolling with it.

He has a seriously impressive resume with great, global experience. And he’s out there continuing to do great things with his online academy.

I hope you enjoy this conversation as much as I did.

So, here it is.

Here is - Peter Wilken. 

In this episode I speak with Hilary Swan.

Hilary is the founder of Rebel Scout Consulting where she supports founders and CEOs as a fractional sales leader. 

From the early days of founder-led sales advisory all the way to a growing sales team in need of leadership and strategy, Hilary has the background, tenure, and nimbleness to hop in and make an immediate impact. 

Hilary and I cover topics including:

And other topics.

This was another conversation I’m grateful for, rich with valuable lessons and takeaways.

Since filming, Hilary had her live event speaking gig and it appears it was a success - so great work Hilary on bringing that to life - you can hear us get into the details of her preparing to speak later in this episode.

So here it is.

Here is - Hilary Swan.

In this episode I speak with Leslie Greenwood.

Leslie is the founder and CEO of Chief Evangelist Consulting, which provides strategic guidance and insights to organizations looking to build impactful communities.

Before starting her consulting company, Leslie was the VP of Member Success & Member Advocacy at Pavilion, where she built the team and programs that drove membership growth from 2k-10k in two years. 

She is also the co-founder of Wednesday Women, an organization that amplifies and spotlights women executives and entrepreneurs. 

Leslie and I cover topics including:

And other topics.

Leslie was great to speak with. We get into her journey, which includes the professional event of at one point being fired - many of us have found ourselves facing that type of event, so you can listen to that chapter of Leslie’s journey in this one.

She was a great guest and, as usual, someone I learned a lot from.

And I think you will too.

Here is - Leslie Greenwood.

In this episode I speak with Gabe Fontana.

Gabe is a solopreneur based out of Vancouver, Canada.

He helps farms and landscaping companies market their products and services online with web design, SEO, and content strategies.

Gabe and I cover topics including:

And other topics.

I love Gabe’s background. You’ll have to listen to the episode to get the full feel for it, but he went from working on a farm to working on his laptop and has picked up really valuable lessons as a solopreneur along the way.

There’s also great analogies to his experience in farming and how he’s now running his own business. The seasons, the patience, the labor - it was a lot of fun to explore with him.

Gabe and I talk a bit about repositioning and I share some details about what I had recently gone through myself in terms of my services and audiences.

All this is to say - this space can move quickly, and I try to keep up with it. So we’ll see how this episode ages and if Gabe and I are still doing in a few months what we’re doing currently.

It was a great episode. I hope you like it. Here is - Gabe Fontana.

In this episode I speak with Chipper Watcott.

Chipper is the Founder of Whelm – a software platform built specifically for solopreneurs and freelancers to take the administrative headache out of doing great work.

He lives in St. George, Utah with his wife, baby boy, and their dog.

Chipper started doing freelance design work in 2017, and launched Whelm in 2023 to address the problems he faced as a solopreneur.

We cover topics including:

And other topics.

I could have kept Chipper on for another several hours. He’s a smart guy with a great story and was a ton of fun to speak with.

And I love that he took his own experience, understood the persistent challenges folks in similar roles face, and is out there building something to address it for today's solopreneurs.

So for all of you freelancers and solopreneurs in the audience - go check out Whelm.

Here is - Chipper Whatcott.