Solopreneur Stories – Details, episodes & analysis

In this episode I speak with Gregory Foran. 

Gregory is the founder of a solo marketing agency called Breakaway Marketing. 

After working in marketing leadership positions for over a decade helping to turn poor performers into market leaders and generating over $129M in incremental revenue, Gregory jumped into entrepreneurship. 

He and I have some very similar stories, which we talk about, including topics such as:

• Scaling a business

• Experiences with subcontractors 

• Family, fatherhood, and taking time off to focus on those things

• Building a niche while being adaptive to market signals

And other topics.

This was a great one, and pretty meaningful for me personally.

I mention pretty early in this episode that I felt like I was talking to my own conscience at a few points. His story and the way he shares it hit me in the chest, and I felt like some of our similar experiences make for some good lessons to anyone listening.

Gregory is a great guy and I’m rooting for him and what he’s building. 

As always it was a great conversation and I learned a lot.

And I think you will too.

Here is - Gregory Foran.

In this episode I speak with Joe Fitzpatrick.

Joe is a fractional CMO who has spent his career working with tech founders who were struggling to attract new customers and who needed to switch their marketing from an ad hoc approach to a strategic, long-term approach.

We cover topics including:

• Understanding the context behind a business’s numbers, and developing strategy beyond a spreadsheet
• The logistical side of running a one person business
• Being the voice of reality for your client
• The challenges of doing marketing for companies that aren’t clear about their broader business strategy
• What Joe has learned on his path of self-employment, including versions of door-to-door sales early in his career and the humbling lessons roles like that can bring

And other topics.

Joe was another great guest - a great guy with a great resume and a great story.

I love his “throw me in and I’ll figure it out” attitude.

I’d encourage listeners to pay attention to his story from his sales roles and how his curiosity and drive made him a top performer. I think anyone listening can extrapolate Joe’s lessons for their own professional journey to bring a willingness to learn and develop opportunities.

So I hope you enjoy listening to my conversation with - Joe Fitzpatrick.

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:

• Superficial brands and substantive brands 

• Branding vs brand strategy 

• Golden handcuffs 

• His experience selling a company 

• Pakistani royalty 

• His experience of writing a book, Dim Sum Strategy - which you should check out

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:

• Figure skating 

• Networking as a solopreneur and asking for referrals and connections

• Fear setting, which is the reverse of goal setting 

• Productized services - which was a healthy discussion

• How Hilary structures her offerings across areas including advisory and fractional engagements

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:

• Putting yourself out there, focusing on what you can control, and allowing the universe to handle the rest

• Curiosity plus action 

• The first live, in person event she put on for Wednesday Women

• The importance of mentors as a solopreneur

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:

• His experience niching as a solopreneur
• Virtual assistants
• Doing cold outreach and business development as a solopreneur
• Working with mentors and coaches as a solopreneur
• Raising your rates as a solopreneur
• Some great resources like the “Build your copywriting podcast” and “the comprehensive copywriting academy”

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:

• Chipper’s experience buying a business
• Urbanism and working from home
• Utah’s tech scene
• Solopreneur side hustles

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.

In this episode I speak with Taylor Crane.

Taylor is the founder of Fractional Jobs, helping startups reach and recruit fractional leaders (think fractional CMOs, CTOs, Heads of Sales, etc.). He's also the founder of Clubs Poker, acquired in 2023, and before that was a Product Manager for 10 years.

Taylor and I cover topics including:

• Quantifiable goals as a solopreneur
• The benefits of fractional work and solopreneurship
• The downsides of fractional work and solopreneurship
• The 40 hour work week and the industrial revolution

And other topics.

My conversation with Taylor was a total delight. I’m fascinated by the concept of work. Why we do it. The way we do it. Anachronisms from culture and history and technology that persist despite there being better options.

Taylor and I cover all of this. It felt like a really fun philosophical exploration of the notion of “work” - and Taylor is building something with Fractional Jobs to walk the walk he believes in, and I admire that with all my love and respect.

He was a great guest, so here he is.

Please enjoy my conversation with - Taylor Crane.

In this episode, I speak with Adam Goyette.

Adam is the founder at Growth Union, a marketing agency that works with growing B2B start-ups to help them scale faster.

He is a former Senior Marketing Executive, who previously led Marketing at Help Scout and Growth at G2 - named one of the Fastest-Growing Private Companies in America by Inc 500 and Deloitte.

We cover topics including:

• Experiencing supportive leaders and CEOs
• Leveraging your network as a solopreneur
• Giving away value as a solopreneur
• Adam’s experiences as a growth advisor and solopreneuer
• Saying no to clients and ending relationships that aren’t working

And other topics.

Confession from me - Adam is someone I’ve been following on social media for a while. I’ve looked up to him for a while, at least in terms of vicariously getting to know him through his posts and comments.

He’s such a great guy. We had audio issues, which were all my fault, and Adam was a total gentleman as I bumbled my way through things.

What Adam is doing with Growth Union is, in my opinion, a real needed shift in the agency and client business model. We get into this in our episode, so you’ll have to check it out, but I’m impressed with what he’s doing and wish him all the best doing it.

So here’s my conversation with - Adam Goyette.

In this episode I speak with Morgan Snyder.

Morgan is the founder of ThoughtLeaderToday.com, where he helps executives tell their story.

We cover topics including:

• Working at a startup
• Defining what you want out of your life
• Surrounding yourself with people doing cool shit
• The challenges of Credentialism in the market as a solopreneur
• Confidence as a solopreneur
• Self discovery, self acceptance, and self compassion

And other topics.

Utah - you have taken the lead with podcast guests reigning from your state. Something about Utah these days, it is cranking out awesome people I have been getting along with.

Speaking with Morgan was a great experience. He’s been on some other podcasts, so definitely check them out. I had before having him on and his personality did not disappoint.

So here it is - please enjoy my conversation with Morgan Snyder.