Imperfect Marketing – Details, episodes & analysis

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In this episode of Imperfect Marketing, I sit down with Jonny Holsten of BridgeSelling to unpack why sales gets such a bad reputation—and how to fix it. We dive into what actually works in modern sales conversations (hint: it’s not scripts or pressure).

Jonny shares his journey from marketing into sales strategy and how that shift led to his book Fix Your Broken Sales Calls. Together, we explore how to move from chasing leads to building meaningful, problem-solving conversations.

Here’s what we cover:

From Leads to “Best Fit” Clients

•  Why all leads are not worth your time 
•  The 4-part framework for identifying a true “best fit” customer 
•  How narrowing your focus actually increases conversions 

Why Sales Feels “Icky” (and How to Fix It)

•  The real reason selling feels uncomfortable for so many people 
•  Why belief in what you’re selling changes everything 
•  The difference between pushing a sale and solving a problem 

The Power of Better Questions

•  How great sales conversations start with curiosity, not pitching 
•  Why most salespeople skip identifying the real problem 
•  A simple technique to get prospects to open up more 

Handling Inbound Leads the Right Way

•  Why inbound leads aren’t always qualified (and that’s okay) 
•  How to guide conversations like a consultant, not a salesperson 
•  The importance of setting expectations and taking control early 

Knowing When to Walk Away

•  How to gracefully exit conversations with poor-fit prospects 
•  Why referring someone elsewhere can actually grow your business 
•  The mindset shift: serving first, selling second 

Improving Sales Without More Leads

•  Why most teams lack a clear plan for sales calls 
•  How small tweaks to discovery calls can drive massive revenue growth 
•  The importance of reviewing and learning from your own calls 

Key Takeaways

•  Selling should feel like helping—not convincing 
•  Clarity in your message makes everything easier 
•  The better your questions, the better your results 

Connect with Jonny:
LinkedIn: https://www.linkedin.com/in/jonnyholsten/

If sales has ever felt uncomfortable, awkward, or forced—this episode will change how you think about it.

Ready to make sales feel natural (and actually work)? Tune in.

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

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In this episode of Imperfect Marketing, I sit down with Stephanie Sylvestre, founder of Avatar Buddy, to explore how AI is reshaping the way businesses operate—and why human skills matter more than ever.

Stephanie shares her fascinating journey from corporate IT leadership to building an AI-powered company, along with the lessons she’s learned along the way (including a few hard-earned ones she hopes you won’t have to repeat).

We dive into how businesses can actually use AI effectively—without losing their values, their culture, or their competitive edge.

In this conversation, we discuss:

The Human Skills That Matter Most in an AI World

•  Why resilience is essential when working with AI (hint: your first output isn’t your best) 
•  How creativity and resourcefulness give you a competitive advantage—especially in fast-changing environments 
•  The critical role of problem-solving and critical thinking when AI sounds right… but isn’t 
•  Why these “human skills” are becoming the real differentiator in an AI-driven world 

Demystifying AI for Businesses

•  What AI agents actually are—and how they can streamline your workflows 
•  How AI can save massive amounts of time when used strategically 
•  Why understanding your data is just as important as understanding the technology 
•  The biggest mistake organizations make when adopting AI too quickly 

Responsible AI: Where Ethics Meet Execution

•  Why responsible AI starts with people—not the technology 
•  How your data directly shapes your AI outcomes (for better or worse) 
•  Practical ways to build ethical guardrails into your AI systems 
•  Why transparency, ownership, and respect for content matter more than ever 

AI, Leadership, and Company Culture

•  How AI can actually strengthen (not weaken) your company culture 
•  Why leaders need to treat AI like any other business initiative—with clear goals and strategy 
•  The importance of starting small, iterating, and evolving your AI implementation 
•  How AI can reduce internal friction and improve team dynamics 

Key Takeaways for Marketers and Leaders

•  You’re not selling AI—you’re selling trust 
•  AI won’t replace people, but people who use AI effectively will have a clear advantage 
•  Your values should guide how you implement and use AI 
•  Success with AI comes from clarity, strategy, and continuous iteration 

Whether you're just starting to explore AI or looking to refine how you’re using it in your business, this episode offers a grounded, practical perspective on what it really takes to succeed.

Are you ready to use AI in a way that actually supports your business—and your values? Tune in to learn how to make AI work with you, not instead of you.

Connect with Stephanie
Website: https://avatarbuddy.co/
Instagram: https://www.instagram.com/avatar_buddyai/
Tiktok: https://www.tiktok.com/@avatar_buddyai?lang=en

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

Watch here

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In this episode of Imperfect Marketing, I sit down with Virginia Elder, podcast strategist and founder of a podcasting-for-business agency. We talk about how podcasting builds trust, drives leads, and becomes a powerful growth tool—without chasing perfection.

We cover:

Why Imperfection Builds Trust

• How over-editing hurts connection
• Why pauses, breaths, and authenticity matter
• The danger of sounding “too polished”

Podcasting for Business (Not Just Downloads)

• Why podcasts should support your core business
• How podcasting turns listeners into leads
• Why sponsorships aren’t the best fit for most service businesses

The C.R.A.F.T. Framework

• Content: Speak directly to your ideal client’s real concerns
• Repurpose: Turn episodes into video clips, emails, blogs, and posts
• Ask: One clear call to action—every time
• Feature: Guests who serve your audience and business goals
• Track: Measure leads, referrals, speaking gigs, and opportunities

Practical Podcasting Advice

• Start monthly if weekly feels overwhelming
• Use tools like Riverside or Descript to simplify production
• Choose a podcast name people actually search for

If you’re using (or considering) a podcast as part of your marketing strategy, this episode will help you stop overthinking and start using it intentionally.

Connect with Virginia Elder:

Website: https://podcastabundance.com/
LinkedIn: https://www.linkedin.com/in/virginiaelder/
Facebook: https://www.facebook.com/podcastabundance

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

Watch here

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In this episode, Kendra Corman explores the humorous and cautionary side of AI in content creation, sharing notable AI blunders and offering practical advice for marketers using AI tools.

Key Takeaways:

• AI can make significant errors, from fabricating legal cases to misinterpreting historical images.
• While useful for idea generation and first drafts, AI requires human oversight and fact-checking.
• AI struggles with context, emotion, and cultural nuances, necessitating human input for sensitive topics.
• Use AI as a tool for inspiration, not as a replacement for human creativity and intelligence.

AI is a powerful tool in marketing, but it's important to use it wisely. Remember: AI is the copilot, not the autopilot, in your content creation journey.

Connect with Kendra Corman:

• LinkedIn
• Kendra Corman's Website

Join us every Tuesday and Thursday for more insights on marketing strategies and building successful businesses. Don't forget to rate and subscribe!

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

Watch here

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Kendra talks imperfect marketing with Kyle Mealy, a dynamic leader, teacher, and speaker who specializes in unlocking trapped potential in entrepreneurial businesses and their leaders. Kyle is a fractional Chief Revenue Officer for small businesses, helping them align their marketing and sales strategies for maximum growth.

Topics covered in today's conversation include:

• The importance of aligning marketing and sales strategies
• How to define and measure profitable return on investment (ROI) for marketing and sales
• The concept of ROASS (Return on All Sales and Marketing Spend)
• Why marketing should be the "tip of the spear" in revenue generation
• The "7x7" rule in marketing: reaching your audience seven times in seven different ways
• How fractional C-suite roles can benefit small businesses
• The challenges of marketing your own business, even as an expert

Resources:

• Traction by Gino Wickman (EOS - Entrepreneurial Operating System): https://www.amazon.com/Traction-Get-Grip-Your-Business/dp/1936661837

Connect with Kyle Mealy:
LinkedIn
Website 

Join us every Tuesday and Thursday for more insights on marketing strategies and building successful businesses. Don't forget to rate and subscribe!

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

Watch here

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In this episode, Kendra Corman discusses the use of AI-powered tools for idea generation, email outlining, and writing. She introduces ChatGPT, Claude.ai, and Perplexity.ai as her favorite AI assistants. These tools can help with generating ideas, structuring email content, overcoming writer's block, conducting research, and experimenting with different tones and styles. 

Highlights:

• AI-powered tools can assist with idea generation, email outlining, and writing.
• ChatGPT, Claude.ai, and Perplexity.ai are useful AI assistants for marketers.
• These tools can help overcome writer's block and provide research assistance.
• Experimenting with different tones and styles can be done using AI tools.
• AI tools should enhance creativity, not replace it.

 AI tools are here to enhance your creativity, not replace it. Start small by incorporating AI into your email marketing process and watch your productivity soar.

Connect with Kendra Corman:

LinkedIn
Website

Join us every Tuesday and Thursday for more insights on marketing strategies and building successful businesses. Don't forget to rate and subscribe!

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

Watch here

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Tom Amate, CEO and co-founder of Entail AI, discusses common organic marketing mistakes and the importance of creating high-quality content. He emphasizes that while AI can be a valuable tool, simply generating content with AI without adding value or differentiation is a mistake. 

Highlights:

• Avoid the mistake of generating content with AI without adding value or differentiation.
• Prioritize SEO and organic marketing by building a proper website and creating high-quality content.
• Streamline content creation and optimize conversion rates with Entail AI's CMS plugin and CRO software.
• Run experiments and test ideas before building them to ensure success in marketing.

Connect with Tom Amitay
LinkedIn
Entail AI

Join us every Tuesday and Thursday for more insights on marketing strategies and building successful businesses. Don't forget to rate and subscribe!

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

Watch here

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Kendra Corman explores email marketing strategies that keep clients engaged and returning for more in this informative episode of Imperfect Marketing.

Highlights:

• The cost advantages of retaining customers versus acquiring new ones
• Techniques for building a quality email list with compelling lead magnets
• How personalization and segmentation enhance email marketing effectiveness
• Essential types of retention emails, including welcome, thank you, and re-engagement messages
• Insights from HubSpot's successful B2B email marketing approach

In the world of marketing, perfection is way overrated. It's all about making genuine connections and providing value.

This episode offers valuable insights for marketers at all levels, demonstrating how to transform your email list into a powerful tool for business growth. Tune in to learn practical strategies for creating an email marketing plan that keeps your customers coming back.

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

Watch here

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In this episode, Kendra Corman sits down with Erin Craske, a leadership and business coach with extensive experience in international multi-level companies, to discuss common mistakes businesses make in marketing and branding.

Erin Craske is the author of a comprehensive book on brand and business strategy, bringing over 20 years of experience to help businesses avoid common pitfalls and achieve sustainable growth.

Highlights:

• The importance of understanding the 'why' behind business issues rather than focusing solely on best practices.
• Why businesses should prioritize long-term profitability over short-term return on investment.
• The dangers of constantly changing directions and how it depletes resources and creates disengagement.
• The critical role of strategy in guiding business decisions and avoiding the 'headless chicken' syndrome.
• The significance of psychology in marketing and understanding customer behavior.

Whether you're a seasoned business owner or just starting out, this episode offers valuable insights into creating a solid brand strategy and avoiding common marketing mistakes. Tune in to learn how to transform your business approach and achieve sustainable success.

Connect with Erin Andrea Craske:

LinkedIn:

Visit Erin's Website for offers: 

• A gift of two full coaching sessions to the listeners
• A 50% discount on the strategy guide - all-in-one marketing toolbox - using EFFORTLESS code at the TGBBS checkout
• Freebies: business surveys, marketing frameworks, quotes, and strategy guide materials

 Join us every Tuesday and Thursday for more insights on marketing strategies and building successful businesses. Don't forget to rate and subscribe!

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

Watch here

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In this episode, Kendra Corman addresses common obstacles and provides actionable strategies to overcome them.

Highlights:

1. Boost open rates with creative subject lines and effective list segmentation.
2. Improve click-through rates by injecting personality and using engaging content.
3. Minimize unsubscribes by setting clear expectations and offering subscription options.
4. Overcome time constraints by prioritizing email marketing and repurposing existing content.
5. Generate fresh ideas by understanding your audience and leveraging storytelling techniques.

Whether you're struggling with open rates, engagement, or finding time for email marketing, this episode offers valuable insights to help you become an email marketing rock star. Tune in to learn how to turn challenges into opportunities for growth and connection with your audience.

Looking to leverage AI? Want better results? Want to think about what you want to leverage?

Check and see how I am using it for FREE on YouTube.

From "Holy cow, it can do that?" to "Wait, how does this work again?" – I've got all your AI curiosities covered. It's the perfect after-podcast snack for your tech-hungry brain.

Watch here