Garrett Jestice, founder of Prelude Marketing, hit a wall of burnout that spurred a dramatic career shift.

In this episode, Garrett talks about his journey from a marketing leader in early-stage B2B software companies to thriving as a solopreneur, navigating the difficult path of client acquisition and scaling a business without scaling time. Garrett shared his insights for solopreneurs on honing sales and writing skills, leveraging networks, and productizing services to stand out in a crowded market. 

(00:00) The two most important solopreneur skills

(01:28) How to navigate the transition to solopreneurship

(05:51) Strategic growth tips for entrepreneurs

(15:18) Transforming fractional CMO role into a productized service

(24:22) Tips to refine the consulting process

(28:06) How to market to different business types

(29:22) Leveraging niche problems to draw in diverse industries

(38:18) How solopreneurs adapt in an oversaturated market

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Follow Garrett on LinkedIn: https://www.linkedin.com/in/garrettjestice/
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Ryan Baum is a growth consultant and content strategist who's redefined his path in the solitude of solopreneurship.

In this episode, Ryan shares his unconventional journey, battling the fast-paced tech industry's "build the plane as you fly it" mentality, and finding clarity through authentic connections and an ADHD realization. From LinkedIn ghostwriting to the intricacies of content operations, Ryan shares his mission to solve real problems for content marketers while fostering meaningful relationships. 

00:00 Marketing that matters

03:06 How cold DMs can build connections

06:54 The journey from in-house to solopreneur

10:01 Slowing down in a fast-paced tech environment

22:18 How to use AI in content creation

35:11 Success using unconventional business models

41:52 Struggles with productized services

55:20 Emotional tolls on content marketers

58:23 The future of SEO and content marketing

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Follow Ryan on LinkedIn: https://www.linkedin.com/in/ryanbaum/
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Tommy Walker is the founder of The Content Studio and he develops content programs for high growth startups and Fortune 1000 enterprises.

In this episode, Tommy shares the struggles he faced, from living in a boarding house with a cracked laptop to scoring a life-changing business opportunity with LinkedIn. He reflects on the highs and lows of transitioning from freelancing to roles at CXL and Shopify, and his eventual pivot to consulting. Tommy discusses the importance of intentionality, the rigors of market research, and the creation of a digital offer ladder.

(00:00) The responsibility of being a solopreneur

(03:36) Starting a business during a recession

(05:10) The struggles of having your first client

(13:14) How to apply acting skills in marketing

(22:28) Building The Content Studio

(28:34) The challenges in building online courses

(31:37) How discontent reports can lead to valuable insights

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Follow Tommy on LinkedIn: https://www.linkedin.com/in/tommyismyname
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Devin Pickell is a solo content and SEO strategist who took the leap into entrepreneurship after being laid off during the 2023 tech layoffs.

In this episode, Devin reflects on his journey from working with big names like G2 and Nextiva to building his own business. He shares the challenges of going solo, the importance of building a reputation versus a personal brand, and how he navigated the ups and downs of solopreneurship. 

(00:00) 2023 tech layoff experience

(01:10) How 'Do I Need SEO?' started

(02:07) Building a network in the tech space

(08:03) The impact of personal branding

(11:25) Going solo as a content and SEO strategist

(19:49) Navigating risk as a solopreneur

(24:29) Leveraging LinkedIn for client acquisition

(32:41) Balancing client work and personal marketing

(45:00) The importance of business strategy and self-promotion

(49:15) The rewarding journey of solopreneurship

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Follow Devin on LinkedIn: https://www.linkedin.com/in/devin-pickell/
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Get my free blueprint for Solopreneurs - ⁠The Digital Consulting Blueprint: 5 Steps To Acquire New Clients, Stabilize Your Income, And Capture The Value You Create⁠: https://becomeadigitalconsultant.com/ 

Bobby Gillespie is the founder of Propr, an advisory and creative services agency he’s run for nine years - he’s currently transitioning to being 100% solo.

In this episode, Bobby reflects on his journey from running an agency to becoming a solo entrepreneur. He shares his emotional challenges, the pressures of market demands, and the transition to advisory and consulting work. Discover Bobby's raw and honest take on the evolving nature of markets, the importance of brand reputation, and why centering on shared principles with customers is crucial.

(00:00) Transitioning to solopreneurship
(02:22) Leaving the big agency life
(04:22) Building a boutique agency
(06:14) The shift to consulting
(09:48) Reflections on the design industry
(18:07) Market perceptions change, strategy is key
(27:53) Giving back to the design industry

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Follow Bobby on LinkedIn: https://www.linkedin.com/in/thatbobbyg/
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Dylan Ciaccio is the Marketing Director of Black Camel Agency and the host of the B2B Strategy Podcast.

In this episode, Dylan talks about transitioning from running the experiment of running something on his own to going back in-house. Dylan shares his insights on aligning incentives, the importance of marketing the problem, and establishing "problemotional advertising." He also opens up about overcoming imposter syndrome, the vital role of mentorship, and his ultimate goal to create a new category in B2B advertising.

(00:00) Dylan’s solopreneur journey

(02:15) The birth of Rekorded

(06:32) Client acquisition and content strategy

(08:12) Existential crisis and category design

(15:22) Transitioning to an in-house role

(24:57) A new perspective with Black Camel Agency

(26:17) The power of ‘problemotional’ advertising

(28:56) Navigating partnership dynamics

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Follow Dylan on LinkedIn: https://www.linkedin.com/in/dylan-ciaccio
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Thom Van Dycke is a certified StoryBrand Guide and business consultant who went through a rocky transition from ministry to entrepreneurship in the midst of the pandemic.

In this episode, Thom opens up about overcoming imposter syndrome and the initial struggles of securing contracts, to eventually becoming a successful coach for solopreneurs.

(00:00) The importance of sales in business

(02:00) Transitioning from pastor to marketing consultant

(05:12) Writing children's books for an NHL agent

(16:02) The role of networking in business growth

(17:57) Adapting and improvising in business

(21:44) The value of giving away knowledge

(28:09) The two reasons why clients don't hire you

(29:21) Marketing vs. sales: key differences

(36:04) Having an abundance mindset in business

(42:31) Balancing family and entrepreneurship

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Follow Thom on LinkedIn: https://www.linkedin.com/in/thom-van-dycke/

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Melanie Deziel is the co-founder of the Creator Kitchen, an author, and a self-described forever student who’s learned a lot in nearly a decade of building a business around herself.

In this episode, Melanie reveals her journey from New York Times big wig to solopreneurship, opening up about the fear of quantifying her worth and navigating business propositions. Melanie discusses her pivot towards content marketing, the creation of "The Content Fuel Framework," and her mission to support undiagnosed autistic women. Tune in for raw insights on partnership diligence, the importance of genuine networking, and how embracing her identity has shaped her passion-driven business.

(00:00) Going from journalist to solopreneur
(04:33) The mental adjustment needed to evaluate your work's worth
(08:43) Recognizing and leveraging opportunities
(11:42) Intentionally pivoting while figuring out preferences and market demand
(21:47) How to access the possibility of a partnership
(24:06) Rebranding handicaps as superpowers
(29:15) Measuring people by yardsticks that don’t belong to them
(34:00) Giving yourself permission to do things that fill your cup
(40:05) What Melanie hasn’t built, yet 

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Follow Melanie on LinkedIn: https://www.linkedin.com/in/melaniedeziel/ 

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Erin Balsa is the founder of Haus of Bold, a content marketing strategist, solopreneur, and mother of three. 

In this episode, Erin shares her journey from SEO-focused writer to thought leadership advocate, the struggles of battling increased competition and dropping lead volume, and the ingenuity behind creating her on-demand course library. 

Nick and Erin talk about the mental toll of solopreneurship, the power of community, and the eternal quest to manage work and life.

(00:00) What actually is thought leadership?
(06:00) Riding the ups and downs of running a business of one
(08:18) Juggling family and work when hitting a low
(15:17) Why networking and finding support is crucial for solopreneurs
(26:06) Supporting execution through people, process, and strategy
(34:04) Understanding and helping others through coaching
(36:59) What Erin’s planning to build

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Follow Erin on LinkedIn: https://www.linkedin.com/in/erinbalsa/

Subscribe to Leading Thoughts: https://hausofbold.com/newsletter/ 

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Bridget Poetker is Founder of Bridget Poetker LLC as well as Founder of Outside, a marketing consultant collective.

In this episode, Bridget shares her journey from ad agency life to falling into tech marketing, the turbulence of layoffs, pay cuts, and finally taking a chance on herself to become a full-time solopreneur.

Nick and Bridget discuss the frustrations of finding the right clients, the importance of recognizing the fit in initial calls, and the internal struggle of aligning personal fulfillment with professional expectations.

(00:00) Unpacking feeling unfulfilled in previous roles

(05:40) What led Bridget to entrepreneurship

(13:45) When leadership’s lack of understanding leads to overwhelm

(18:39) Big concerns about going out on your own

(25:43) Prioritizing reputation, not brand

(30:20) Embracing flexibility in work hours

(35:11) The challenges of not feeling safe or appreciated

(42:09) The value of collaboration and working with friends in an industry

(49:59) Picking clients through shared mindsets 

(55:27) Building a client base through referrals and inbound marketing

(59:27) Balancing professional and personal identity

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Follow Bridget on LinkedIn: https://www.linkedin.com/in/bridgetpoetker/ 

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Get my free blueprint for Solopreneurs - ⁠The Digital Consulting Blueprint: 5 Steps To Acquire New Clients, Stabilize Your Income, And Capture The Value You Create⁠: https://becomeadigitalconsultant.com/