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Solopreneur Stories
Will Stevens
50 episodes
5 days ago
Solopreneur Stories is the podcast that examines the best insights other solopreneurs have already figured out so you can use them in your life.
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Entrepreneurship
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All content for Solopreneur Stories is the property of Will Stevens and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Solopreneur Stories is the podcast that examines the best insights other solopreneurs have already figured out so you can use them in your life.
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Entrepreneurship
Business
Episodes (20/50)
Solopreneur Stories
Family, fatherhood, freedom, and finding focus as a solopreneur

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.

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11 months ago
1 hour 2 minutes 28 seconds

Solopreneur Stories
Sales, solopreneur strategies, and self-employed success

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.

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12 months ago
1 hour 9 minutes 18 seconds

Solopreneur Stories
Strategy, systems that stick, and success as a solopreneur

In this episode I speak with Trent Warner.


Trent is a fractional CMO and the managing director of Strategic Brand Builders. Where he focuses on bringing marketing strategy and systems into businesses to create clear and consistent growth - not marketing whack-a-mole. 


We cover topics including:


  • Some of the problems with the agency model of today 

  • Having high expectations of yourself 

  • Trust, the currency of relationships 

  • The importance of strategy

  • Working remotely and the ‘return to the office’ collision

  • Establishing strategies and systems 


And other great topics.


Trent is an old colleague from a lifetime ago, so it was great to reconnect with him and hear about all of the great stuff he’s doing. 


I was personally able to learn some pretty tactical things as takeaways from my conversation with Trent, and I’m betting for other solopreneurs out there you’ll find the same.


So don’t miss this one.


Here is - Trent Warner.

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1 year ago
1 hour 18 minutes 26 seconds

Solopreneur Stories
Ergonomics, executing customer success strategies, and entering the enterprise of solopreneurship

In this episode I speak with Parul Bhandari.


Parul is a Customer Success startup advisor and consultant.  


Following a career in ergonomics consulting and in HR, Parul launched her first Customer Success (CS) team from the ground up, and from then on has focused on driving startup Customer Success journeys.  


In addition to Customer Success, she is a passionate advocate of all things food and fitness, and of promoting DE&I.


We covered topics including:


  • Her initial path to becoming a doctor 

  • Ergonomics 

  • The “build phase” of companies 

  • Launching a community

  • Being a contributor for online publications like Inc.

  • The importance of documentation 


And other topics.


It was great to speak with someone in the customer success space. We get into the importance of its function and contributing to revenue in businesses, from hiring to developing and other details that can bring this function to life. 


If you’re in that space or working with them, you’ll definitely learn some things from Parul.


So here she is.


Here’s my conversation with - Parul Bhandari.

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1 year ago
1 hour 1 minute 2 seconds

Solopreneur Stories
Self-advocacy, speaking from the stage, and the secrets to success as a solopreneur

In this episode I speak with Shailvi Wakhlu.


Shailvi is a seasoned Data Leader and Self-Advocacy Expert with over sixteen years of experience building technology products. 


She has spoken at nearly 100 global conferences and Fortune 500 events, coached close to 500 individuals, and authored the best-selling book "Self-Advocacy." Which I’ve read and would recommend you read, too.


Her career includes notable roles at Salesforce, Fitbit, and as the Head of Data at Strava.


We cover topics including:


  • Her experience writing her best selling book, and the supporting speaking engagements she’s done

  • The topic of self-advocacy, which I think a lot of listeners will get a lot of value out of 

  • Her experience building an online course 

And other topics.


It was a great conversation. Her passion for self-advocacy really comes through. The word authenticity gets thrown around a lot, but when you speak with someone like Shailvi you can really connect with how genuine she is for the work she’s doing and why she’s doing it.


I learned a lot. And I think you will too.


Here is - Shailvi Wakhlu.

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1 year ago
1 hour 1 minute 39 seconds

Solopreneur Stories
Data dilemmas, digital decisions, and being a dad as a solopreneur

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:


  • Fatherhood and family 

  • Data vs. insights 

  • Qanon, 4chan, and shady website data 

  • Leveraging AI

  • Setting your own boundaries 


And other topics.


Please enjoy my conversation with - Michael Strachan.

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1 year ago
57 minutes 17 seconds

Solopreneur Stories
Solopreneur strategies, shifting priorities, and setting yourself up for success for your one person business

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:


  • Hiring more people to grow - which puts you in whole new area essentially running an agency

  • Niching even further and trying to become more of an expert in a single function

  • Do nothing and continuing on the path you’re on


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.

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1 year ago
1 hour 27 seconds

Solopreneur Stories
Freelancing, friendships, and fresh perspectives

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:


  • Working with a business coach as a solopreneur

  • Healthy outside perspectives 

  • Perseverance vs stubbornness 

  • Developing honest internal signals and learning how to trust yourself 

  • Comparison and how to avoid comparing your own joy away


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.

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1 year ago
1 hour 4 minutes 7 seconds

Solopreneur Stories
Fractional ABM, financial independence, and freelance strategy as a solopreneur

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:


  • Being a working parent
  • Freelancing and focusing on your craft as a solopreneur
  • The FIRE retire early movement
  • Overemployment
  • Organization as a solopreneur
  • The details of fractional engagements


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.

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1 year ago
1 hour 10 minutes 44 seconds

Solopreneur Stories
Honoring what's important, hourly rates, and helping startups as a solopreneur

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:


  • Being intentional with one’s time as a solopreneur

  • Identifying what’s important in one’s life and honoring it

  • Why Gargi is comfortable billing hourly - something that, at least at the time I’m filming this, I am also comfortable with under certain conditions

  • Networking events and professional growth as a solopreneur


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.

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1 year ago
56 minutes 54 seconds

Solopreneur Stories
Strategy, selling companies, and stories of solopreneurship

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. 

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1 year ago
1 hour 7 minutes 11 seconds

Solopreneur Stories
Fractional sales leadership, fear setting, and figuring out your path as a solopreneur

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.

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1 year ago
1 hour 6 minutes 4 seconds

Solopreneur Stories
Evangelism, events, and earning clients as a solopreneur

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.

Show more...
1 year ago
56 minutes 54 seconds

Solopreneur Stories
Farming, freelancing, and finding your way as a solopreneur

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.

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1 year ago
57 minutes 54 seconds

Solopreneur Stories
Whelm, work, and the wild world of freelancing and solopreneurship

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.

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1 year ago
1 hour 5 minutes 15 seconds

Solopreneur Stories
Fractional jobs, finding meaningful work, and the future of solopreneurship

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.

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1 year ago
56 minutes 29 seconds

Solopreneur Stories
Growth Union, giving value, and going all in as a solopreneur

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.

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1 year ago
1 hour 1 minute 3 seconds

Solopreneur Stories
Thought leadership, thoughtful ventures, and thinking about what you want out of life

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.

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1 year ago
1 hour 18 minutes 11 seconds

Solopreneur Stories
Family, fractionals, and finding your path as a solopreneur

In this episode I speak with Neil Weitzman.


Neil is the founder of revenue•x, a revenue advisory providing fractional CRO services.


Neil helps early-stage ​and medium-sized businesses build and grow. CEOs call Neil when ok is not good enough.


We cover topics including:


  • Family
  • What makes a good fractional leader
  • Companies learning from the mistakes of the market
  • Hiring fractionals before departments
  • How tactical should fractionals get
  • The art of expectation setting


And other topics.


Neil is an impressive guy. He’s someone I look up to as a voice in the fractional space and the great work he’s doing building a community, Porch, which you’ll hear about in our episode together.


Thank you Neil for all of the great information. Neil is someone who for me personally, amidst all of the noise one may encounter on social media, always stands out as having something interesting to say and add to the conversation.


And I’m grateful that part of that conversation is what I’m bringing you with this episode.


So here it is.


Here is - Neil Weitzman.

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1 year ago
58 minutes 2 seconds

Solopreneur Stories
Demand gen, determination, and diving into solopreneurship

In this episode I speak with Tory Kindlick.


Tory is the founder of Growth Trajectory, a growth marketing consulting company.


Prior to his move into the world of solopreneurship, Tory worked as VP of Marketing at Corti (a Healthcare AI company) and Refine Labs (a full-service Demand Gen agency), as well as several demand gen leadership positions at B2B SaaS start-up's.


Tory's super power is "figure-it-out-ability", and he's always ready to shift into problem solving mode when his clients or network of B2B marketers need help with GTM motions, RevOps, or customer acquisition strategies.


We cover topics including:


  • Sharing your work in the open as a solopreneur
  • Adjusting to working as a solopreneur and developing a rhythm to running your business
  • Imposter syndrome, which I think to date every guest has experienced some form of
  • Leadership
  • Incremental improvements as a solopreneur


And other topics.


Tory was another fun guest. I learn a lot from everyone I speak with on this show and Tory was no exception - he’s a great guy with a great attitude and it was a total pleasure having him on and hearing his story.


So here it is.


Here is - Tory Kindlick.

Show more...
1 year ago
59 minutes 54 seconds

Solopreneur Stories
Solopreneur Stories is the podcast that examines the best insights other solopreneurs have already figured out so you can use them in your life.