EP - 001

How to Overcome Sales Anxiety

With Guest Jeff Lerner

Jeff Lerner, the mastermind behind Entre Institute, shares how to reframe sales to eliminate the anxiety that often comes with the role. Uncover strategies that can propel your sales success.

The How To Sell More Podcast


September 11, 2023

In today's episode, we talk about sales anxiety. Our guest is Jeff Lerner, the man who went from a broke jazz musician to a hundred million dollars in online sales. Today, Jeff is the leader of Entre Institute and Max Rev, two companies that help entrepreneurs sell more.

Jeff shares why being genuine and honest is critical to selling well. He believes sales is not just about selling things, but also building authentic relationships. Let's dive in and learn more about the heart of selling.

Key Takeaways

  • Authenticity in sales is the foundation of lasting relationships and genuine customer loyalty.
  • A sale isn't just a transaction; it's an opportunity to solve a problem and make a difference.
  • Resilience in the face of rejection is a salesperson's greatest asset, turning challenges into learning opportunities.

Top 3 Reasons to Listen

The Authenticity Factor: Discover the unparalleled importance of authenticity in sales and how it can be the game-changer for building lasting customer relationships.

Value-Driven Conversations: The episode focuses not just on sales techniques but also on the values and principles that drive successful sales interactions.

Expert Insights: Gain knowledge from Jeff Lerner, a renowned entrepreneur and sales expert, as he shares his rich experiences.

Links to This Episode

Follow Jeff on Social

IG: @jefflernerofficial

Youtube: @JeffLernerofficial

More About Today's Guest, Jeff Lerner

Entrepreneur, Musician, Author, Podcaster, Husband, Father

From broke jazz musician to $100 million in online sales… Jeff Lerner’s story, and social media reach have inspired millions to get control of their future and reshape their life around his "3 Ps of Success" (Physical, Personal, & Professional).

After a decade of building multiple businesses to over 8 figures and twice landing on the INC 5000 Jeff turned his focus to building the worlds first institute of higher learning exclusively for entrepreneurs. In 2019 he founded ENTRE Institute where over 150,000 students have learned the best ways to build a business in the modern world and which became Jeff's 2nd INC 5000 company (and 3rd appearance on the list).

In 2021 Jeff set his sights on solving one of his students’ biggest pain points and launched Entresoft which fast became one of the most popular small business software suites on the Internet.

Jeff’s interest in entrepreneurship began in his 20s when as a pianist he was often hired to play in the homes of successful CEOs and business owners. In 2008, at age 29, after multiple failed ventures, including a restaurant franchise that left him with a half million dollars in debt, he found his first success online and paid off the debt in 18 months.

He currently maintains an active schedule of speaking events and media appearances while working day-to-day in ENTRE, hosting a top 100 business podcast, growing his YouTube channel, and working on his first full-length book “Escaping The Broken System” which is scheduled to publish by BenBella Books in Fall 2022.

He is married, an active father to 4 children, and still enjoys playing the piano 1 hour per day...

A Transcription of The Talk

Mark Drager: So, Jeff, in your business experience, you've built up Entre Institute, which is on pace to hit $100 million in annual revenue, which is massive. But you also own this other business, where you're a partner, that helps run sales floors. I think you're uniquely positioned because your background is in marketing. What challenges have you experienced and helped others overcome when connecting what marketing does with what sales need to close?

Jeff Lerner: I love that question. I'll provide a bit of context first. We were a completely bootstrapped company. I started it with a $20,000 budget on a credit card. As you mentioned, we're on pace to hit $100 million in annual revenue in the next 12 to 18 months. It's a remarkable success story. I had to learn about scrappy, bootstrapping-type marketing that would directly lead to sales. Being a bootstrapped company gave us a scrappy, sales-focused ethos. We believe that it's essential to convert clicks and eyeballs into dollars, especially when you're bootstrapped and on borrowed time.

Now, as we grow, we're hiring people from the VC-backed world. They don't have the same urgency we have, like "if I don't make a sale today, I won't eat tonight." They come from environments like "we're burning through our Series B funding." This has created a tension internally. Some want to focus on brand-building and storytelling, while others, like me, feel the urge to sell immediately. While this urgency may not be as relevant now, it's hard for me to let go of those habits.

In Max Rev, our sales service company, we often discuss this with marketers and entrepreneurs. We understand that they love their products and might want to talk about their value all day. But if no one is buying, the product won't survive. There's a trend where some marketers are almost embarrassed to overtly sell their beloved products. However, every business needs sales to thrive.

To start, it's crucial to have a philosophical check with people about their views on selling. Do they think selling is vital? Can they get excited about it? While this show is tactical, and we'll get into tactics, in my experience working with different clients through Max Rev, we often have to challenge their mindset. Some don't want to admit that they might be lacking in sales because they're not passionate about it. But until that's addressed, results won't change. So, for the audience, I hope you're enthusiastic about selling. If not, that's a deeper issue that needs resolution.

Mark Drager: I want to jump in real quick on that. You know, I had a friend who was writing a book, and I asked, "Why are you writing the book?" He said, "I need the book for my email content." I was confused and asked, "So you're turning each chapter of your book into email content? What's the purpose of the email?" He responded, "I haven't launched because I haven't written the book." I asked, "How many people are on the list?" He hadn't created that yet. So I tried to understand, "You're writing the book to feed your email, and then the email will build the list? Who's going on the email?" He said he needed to create an offer. I asked if he'd done that, and he said no. I inquired about how he'd promote the offer, and he mentioned social media. When I asked about his followers, he admitted he hadn't built his social media presence yet. Trying to get to the root of it, I asked, "Why are you doing all this?" He said, "So I can get clients." I pointed out that he could just talk to people about what he's doing. He wanted to run a coaching program, and I felt he was going in circles. I told him, "You could spend the next nine months doing all this to get clients. Why don't you just tell people what you do, who you can help, and say, 'I will help you with your problem. I'll take responsibility.'" I believe sometimes people, including myself, are afraid. He might have been scared to either promote his service or to take ownership of someone else's issues. So, we end up getting lost in tasks that seem essential when we could just communicate directly with potential clients.

Jeff Lerner: That's so true. It's like the inverse of the sales mentality where people opt for the heaviest tasks that produce the lowest yield first. This mindset really gets to the heart of sales. 

Absolutely. Like we discussed before the show, the concept of pre-revenue companies is, in my opinion, an oxymoron. What exists pre-revenue is just an idea, maybe a somewhat operationalized idea. It's not a business. It's not a company until there's revenue, right? Nothing happens until something gets sold. I should clarify, for the rest of this conversation, that I have no formal training as a salesperson. I don't have traditional sales credentials, but I've sold almost $200 million in products online. So I suppose that counts for something.

Mark Drager: To give our listeners some context, you are a professional jazz musician, right? So, your background isn't in corporate or sales at all.

Jeff Lerner: Right, exactly. I was a professional jazz musician, occasionally dabbling in musical theater, and had an entrepreneurial spirit. I primarily delved into entrepreneurship because I played at these affluent people's homes, performing piano. I would think, "Who are these people?" They seemed just as free as I was, doing what they wanted, yet they owned their luxurious homes, while I was struggling with rent. Their pianos alone were worth more than everything I had. I soon realized they were entrepreneurs or company founders who could afford my services for their dinner parties. That's how I got intrigued by entrepreneurship. 

To clarify, when I started, I transitioned from simply being interested in entrepreneurship to diving all in. The reason was a massive debt. By my late 20s, I was about $495,000 in debt because I tried to juggle my passion with part-time entrepreneurship. I'd borrowed excessively to open up franchise restaurants, even without prior entrepreneurial success. It was a questionable decision by both the bank and me, a jazz musician. The timing was unfortunate, opening them in 2007 just before the recession. So there I was, a 29-year-old jazz musician, half a million dollars in debt. 

I turned to the online world, learning about affiliate marketing. Initially, I was promoting products with small commissions, thinking it would take forever to clear my debt this way. I then found programs with large commission potentials. However, selling these wasn't as straightforward as posting content with a link. I had to actively engage, even getting on the phone with prospects. As a tactical suggestion, are businesses capturing phone numbers from their leads? Many just capture names and emails, fearing that adding a phone field might reduce opt-ins. But there's a bigger picture to consider. Capturing phone numbers might reduce the list size, but the potential revenue from direct phone engagements can be exponentially higher than just email.

Mark Drager: Studies show that, generationally, younger millennials and Gen Z's prefer text over email. Businesses need to adapt to this shift. Especially in B2B, potential clients in the research phase often want direct communication. Older generations might prefer phone conversations, while younger ones might ignore emails altogether. Recognizing these changing preferences and tracking them can significantly impact sales outcomes.

Jeff Lerner: I believe that being effective on the phone isn't exclusive to B2B. In modern B2C, it might be more challenging to get someone on the phone, but once you do, it's just as impactful. Returning to my story, when I began capturing phone numbers and calling people, my approach was very direct. Instead of sending emails promoting a product, I'd introduce myself as the person behind the page they opted into. Now, I had no formal sales training, but being a jazz musician made me an expressive and open individual. I'd connect with these leads, explaining my background and being candid about my situation. I'd tell them I was a jazz musician, and given the online education products I promoted were in business, wealth creation, or investing, it was evident they were interested in making more money. I'd joke, saying if there's anyone who needs more money, it's a jazz musician, and delve into how I might be able to help them. My conversational style was very relaxed, and I'd let them talk, breaking many traditional sales rules. One memorable interaction was with an RV park owner in Arizona. By the end of our chat, he said I was the first person he'd actually spoken to online, and he ended up purchasing a $13,000 program, earning me a $4,500 commission. This was a pivotal moment for me. I realized sales wasn't about following a strict script but genuine human connection with an earnest desire to help and solve problems. Sometimes, I think we overcomplicate sales. At its core, it's about human connection.

Mark Drager: Earlier, you mentioned that many entrepreneurs and businesses you work with seem to shy away from embracing sales. What would you recommend? If you were to diagnose our collective aversion to sales, how would you advise us to overcome it? We might not like the answer, but we need to hear it. Give us the raw truth.

Jeff Lerner: I was contemplating this recently: the human brain is inherently a normalizing machine. Over time, we become accustomed to almost anything. I had a conversation with someone about content creation, and they expressed how challenging it is to stand in front of a camera and articulate their thoughts. I empathized, acknowledging that yes, it's a difficult task. However, I suggested they commit to turning on a camera twice a day for 15 minutes, standing in front of it, and just speaking. Whatever emerges is okay, and there's no obligation to publish it. But by regularly practicing, they'd develop the skill and become more comfortable. When I was younger, I despised brushing my teeth. It felt like a daunting chore. Now, I don't think twice about it and brush religiously. The solution to becoming proficient at sales is to engage in conversations about your offerings and actively pitch them. By consistently making offers and seeking potential buyers, you become more adept at it. Industry experts like Frank Kern advocate making an offer every day. Dan Kennedy says if your marketing hasn't ruffled some feathers by noon, you're not marketing aggressively enough. The main hurdle isn't acquiring the skill set; it's acknowledging the significance of sales and being committed to the process. I don't believe anyone is inherently bad at sales. It's more about openness to its importance and the willingness to practice.

Mark Drager: You touched upon a pivotal moment when you earned a $4,500 commission from a simple phone conversation. This approach might be feasible on a small scale or during initial stages when one has abundant time. However, it doesn't seem scalable for larger businesses. It's unrealistic for a company to suggest that everyone just hop on the phone indefinitely. Or is it? Are we overthinking and over-engineering the process?

Jeff Lerner: Absolutely, my approach was unsophisticated. Spending hours on the phone, letting people speak without interruption, isn't scalable. However, I've always been transparent about my passion for sales. Anyone who engages with my content shouldn't be surprised when I pitch something to them. They know I view entrepreneurship as a fierce battle. While it's not necessarily a zero-sum game like gladiator combat, the idea is to shed the hesitation and be direct. In today's world, people are overly cautious about not offending anyone, making them hesitant about sales. But with the right marketing journey, you prepare your audience for a sales pitch. It doesn't come as a shock, nor is it incongruent with the brand. If your brand struggles with converting sales, then it's a weak brand. Good branding ensures that when it's time for the sales pitch, it's not awkward but rather an expected and enjoyable part of the process. It becomes a light-hearted conversation where the potential client knows the value and is eager to buy.

Mark Drager: You've painted it in such a hyperbolic manner that it becomes almost ridiculous not to proceed.

Jeff Lerner: I recently reintroduced a personal coaching offer on my website. In the past, I did a lot of coaching, but now, due to time constraints, I do very little. However, I genuinely enjoy it. So, I've limited my availability to just two hours a week, specifically on weekends. I'm passionate about coaching, and while I'm not driven by the money, I also won't offer it for free.

Mark Drager: That's a clever use of scarcity tactics.

Jeff Lerner: Yes, I'll admit, that's a form of scarcity. But it's genuine scarcity. I truly only have two hours a week for this. While it might not be worth my time from a monetary perspective, I do it because I genuinely enjoy it. It's a valuable angle for positioning. I recently had a conversation with someone I know quite well. I made it clear that we could discuss his project once for free, but any subsequent consultations would be charged. He understood and even booked a paid session after our first chat. People get nervous about selling, which is ironic because everyone's paycheck is funded by the sales of their company's products.

Mark Drager: That's precisely why we're discussing this on the podcast. Sales is the key driver for businesses. Everything, from profits, revenue, R&D, to hiring staff, hinges on sales. So, Jeff, as we wrap up, what's your top recommendation or strategy for our listeners when it comes to boosting sales?

Jeff Lerner: My main advice revolves around branding and marketing content. Be forthright with your value proposition. Ensure that your audience understands what they receive for free versus what they'll get when they pay. Businesses should understand the principle of giving before asking. Clearly define the relationship customers have with your brand when it's free and when it's paid. In my line of work, the education sector, I emphasize that while information might be free or very cheap, transformation comes at a price. If someone approaches me saying they've consumed my free content and now need help implementing it, I clarify that they're transitioning from information to transformation, and there's a cost associated with that.