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Inside the Speakeasy Podcast - Your Key to Hidden Strategies & Success Stories from Top Entrepreneurs

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Inside the Speakeasy Podcast - Your Key to Hidden Strategies & Success Stories from Top Entrepreneurs

Sam Wakefield on How Confidence in One’s Identity Drives Real Sales Conversions

January 06, 2026 • Speakeasy Mastermind • Season 1 • Episode 37

Selling gets a lot simpler when people feel like they’re choosing you, and not being sold to. In this conversation, we talk about how identity and authenticity quietly do the heavy lifting in sales, building trust before price ever comes up. It’s a real look at how you can close more deals without pressure, scripts, or that “salesy” feeling.

Sam Wakefield, Sales Expert, International Bestselling Author, Speaker, and Host of the Close It Now Podcast, brings nearly two decades of hands-on experience from the home services world. He shares how he went from working in the field to growing businesses without spending money on traditional marketing, leaning instead on podcasting, community presence, and smart guerrilla marketing. The heart of his approach is simple: become someone worth buying from and let that do the work.

We also get into Sam’s Wheel of Success, practical ways to get noticed locally without blowing your budget, and how he grew his podcast into the top 1.5% globally with consistency and clarity. If you want more natural sales conversations, stronger confidence, and better connections with customers, this episode delivers. Inside the Speakeasy Podcast is brought to you by Go High Level, the AI-powered business operating system trusted by over 2 million businesses to automate, scale, and create real leverage. Grab an exclusive 30-day trial at https://gohighlevel.com/speakeasy-mastermind-promo.

Key Timestamps:

[00:00:00] Introduction.

[00:02:32] Journey towards becoming a sales expert.

[00:09:00] Are you worth buying from?

[00:12:39] The Wheel of Success.

[00:21:11] Self-audit for personal improvement.

[00:23:12] Lead generation strategy.

[00:25:30] Podcasting tips for beginners.

[00:30:54] Free guerrilla marketing guide.

[00:35:25] Personal growth drives business success.

[00:36:39] Arch nemesis: best version of yourself.

Memorable Quotes: