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Artwork for How to Win BIG at Business

How to Win BIG at Business

Joe DiChiara
Artificial Intelligence
Small Business
Cash Flow
Positioning
Pricing Strategy
Recurring Revenue
Philippines
CFO
Prompt Engineering
Avatar / Ideal Client
S Corporation
Personal Budget
Revenue Peaks and Valleys
Payment Terms
Self-Employed Professionals
IRS
Sole Proprietorship
C Corporation
Sales Funnel
Lead Generation

Being a solopreneur or small business owner isn’t easy—you’re wearing all the hats, managing clients, handling finances, and trying to grow without burning out. That’s where this podcast comes in.

Hosted by Joe DiChiara, CPA, entrepreneur, and business mentor, How to Win BIG at Business delivers straight talk, practical strategies, and real stories that help you cut through the noise and focus on ... more

PublishesWeeklyEpisodes27Founded6 months ago
Number of ListenersCategories
EntrepreneurshipBusiness

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Artwork for How to Win BIG at Business

Latest Episodes

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The IRS may be quiet right now, but Joe DiChiara warns business owners not to get too comfortable.

In this episode of How to Win Big at Business, Joe explains why the next wave of IRS audits may look very different from the old day... more

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If AI has you overwhelmed, this episode will help you stop spinning, focus on what matters, and start using it in a way that actually helps your business.

You are not alone.

In this episode of How to Win Big at Business, Joe DiChi... more

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If you’re a self-employed professional still doing everything yourself, this episode is for you.

For years, business owners have said, “You just can’t find good help anymore.” But in this episode of How to Win Big at Business, Joe ... more

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Success on the outside does not always mean peace on the inside.

In this episode of How to Win Big at Business, Joe sits down with therapist and self-employed professional Tara Larchemar for a powerful conversation about what many ... more

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What do you do when life changes in an instant?

In this powerful episode of How to Win Big at Business, Joe DiChiara sits down with Vincent Lanci — author, podcaster, coach, entrepreneur, and traumatic brain injury survivor — to ta... more

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Most business owners think they know their numbers — but if you’re only watching sales and your bank balance, you could be making decisions based on the wrong information.

They are either tracking nothing or tracking the wrong thin... more

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What if the biggest financial mistake small business owners are making is relying on numbers that are already too old to help them? 

In this episode of How to Win Big at Business, Joe breaks down why the role of the CFO is becoming... more

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In this episode of How to Win Big at Business, Joe DiChiara sits down with entrepreneur and technology expert Jerry Goddard to talk about a problem almost every self-employed professional is facing right now: AI overwhelm.

If you f... more

Key Facts

Accepts Guests
Contact Information
Podcast Host
Number of Listeners
Find out how many people listen to this podcast per episode and each month.

Recent Guests

Nick Petras
Founder of HireFreely, builder of Rocket training program
HireFreely
Episode: Still Doing Everything Yourself? This May Be Why You’re Stuck
Tara Maddy Larchemar
Therapist and holistic practitioner featured on the episode
Inner Light Integrative Therapy / healinginnerlight.com
Episode: Why So Many Entrepreneurs Look Successful but Feel Disconnected
Vincent Lanci
TBI world-renowned expert, best-selling author, podcaster, and coach
Self-employed/Author/Podcaster
Episode: He Woke Up From a Coma and Rebuilt His Life From Scratch Episode
Jerry Goddard
Serial entrepreneur in technology, cybersecurity and military intelligence; former Marine
Redbeard Solutions
Episode: Overwhelmed by AI Tools? How Self-Employed Professionals Can Use Google Notebook LM
Marianne Labonete
Coach Yanyan, LinkedIn top 100 Philippine influencer and founder of TaskWise/Coach Yanyan
Bedrock (collaboration) and various coaching/affiliate initiatives
Episode: The Freedom Formula: Strengths, Visibility, and the Right Business Model
Marge Aviso
Owner of Telework, a large BPO in the Philippines
Telework (Philippines) / BPO
Episode: From Nurse to Entrepreneur: Marge Aviso’s Journey to 1,600 Employees

Host

Joe DiChiara
Host of How to Win BIG at Business

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Top Entrepreneurship Podcasts

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Proven PodcastCharles Schwartz
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Young and Profiting with Hala TahaHala Taha | Entrepreneurship, Sales, Marketing | YAP Media Network
The Money Mondays
The Money MondaysDan Fleyshman
Creating Confidence with Heather Monahan
Creating Confidence with Heather MonahanHeather Monahan | YAP Media

Talking Points

Recent interactions between the hosts and their guests.

Still Doing Everything Yourself? This May Be Why You’re Stuck
Q: What makes Freely different from other freelancing platforms?
It's built around skills and live interactions, uses an algorithm to match based on demonstrated strengths, limits connections to three to maintain quality, and ensures fast, direct conversations with a pay-for-interview model that refunds if no interview occurs.
Still Doing Everything Yourself? This May Be Why You’re Stuck
Q: How does Freely actually work when a company needs a particular skill like a website designer?
Freely focuses on skill descriptions rather than resumes; it surfaces the top three available matches, then the company engages with them directly, streamlining the process and bypassing traditional resume-driven filtering.
Overwhelmed by AI Tools? How Self-Employed Professionals Can Use Google Notebook LM
Q: How is NotebookLM different from ChatGPT or other LLMs?
NotebookLM only draws from the input data you attach to it, rather than the entire internet, making its responses more grounded in your own materials. It also offers various export formats and the ability to generate outputs like flashcards, quizzes, slides, or even a website from your content.

Audience Metrics

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Listeners per Episode
Gender Skew
Location
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Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About How to Win BIG at Business

What is How to Win BIG at Business about and what kind of topics does it cover?

This show consistently leans into practical, no-nonsense guidance for solopreneurs and small-business leaders. Episodes frequently cover finance and pricing strategies, cash flow discipline, and the evolving role of AI and automation in daily operations. There's a strong emphasis on hiring effectively, outsourcing, and building scalable systems—from fractional CFO approaches to skills-based marketplaces and remote work ecosystems—often paired with real-world anecdotes and step-by-step frameworks. A notable strength is translating complex topics (tax, finance, AI, marketing) into actionable playbooks that listeners can implement to cut friction and grow with less burnout. The format often features a seasoned host sharing personal experiences... more

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How many episodes of How to Win BIG at Business are there?

How to Win BIG at Business launched 6 months ago and published 27 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact How to Win BIG at Business?

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What guests have appeared on How to Win BIG at Business?

Recent guests on How to Win BIG at Business include:

1. Nick Petras
2. Tara Maddy Larchemar
3. Vincent Lanci
4. Jerry Goddard
5. Marianne Labonete
6. Marge Aviso

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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