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Deeper Business

Deeper Business

Jessica Lackey | Harvard MBA turned Small Business Strategist

Build your business - and your business-building intuition with foundational frameworks and practical application.

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Feb 23 • 4 min read

How 'Frank' turned a "No" into a $7,000 sale

When I started in this online entrepreneurship journey, I was told that the way to "sell" was to make lots of broadcast content, hope something hit a pain point, and that potential clients would reach out to book a call or buy my course.

Well if you haven't figured it out by now... that's not really working for us anymore.

I believe the days of "passive" sales have passed, at least for service providers.

There's more noise than ever on social, and on email.

Someone posted something cool on LinkedIn? If I click away, then the post goes away and I have to remember to search for it.

Even for things I want to do - things I've committed to say yes to, things I've signed contracts for - sometimes I get distracted AS I'M MAKING A PAYMENT and don't finish and need to be prompted.

I need routine reminders and nudges for things... especially when time has gone by and then I get embarrassed that I didn't respond to their original email.

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Now I love showing up in your email inbox every week and I think it's important to be that presence that shows up regularly as a reminder that you're there. (Although, monthly works too!).

But your busy prospects, and heck even your clients don't read all of your messages, and it's not personal! A number of my clients don't know I have a podcast or a YouTube channel. There's just too much information, too many emails, and if your email happens to arrive on a prospect's desk when they are home with their kids during a snowstorm? Who knows when that email gets replied to.

And sure, if you have a large enough audience, you probably can still make the sales you need to make. But I'm not willing to take that chance... are you?

Be the pattern interrupt.

In this environment, what's passive often just fits into the daily cacophony of our lives.

But when you're proactive? When you're actively showing up in someone's field and interrupting the pattern with something intriguing or something personal?

They might lean in. You might have broken through the noise.

Be personal. Be proactive. Deepen the relationship with your key prospects, partners, and potential clients (and active ones too) at every turn. Reach out regularly, and don't wait for the algorithm to do it for you.

This is the role of an active sales process.

How 'Frank' turned a "No" into a $7,000 opportunity:

Normally, I don't make clickbait-y YouTube videos. But in this one, take guidance from Frank as the "no" started a new conversation, in a generative way for the prospective client.

Deeper Foundations registration ends soon.

Ditch the tactics that aren't working in this economy and develop solid business foundations. Get my expert eyes on your positioning, offer structure, and marketing and sales activities. With live calls 2x a week and a small group, you won't be lost in a crowd or left to your own with a course.

We start March 13 and run through August. Only 2 spots remaining, with registration closing March 4. Please email if you're interested or have questions.

NEW EPISODES

Depth as a Feature, Not a Bug: Winning clients through genuine care with Jeremy Enns

Almost every single business coach, friend, and mentor, has given Jeremy the same piece of advice when they hear about how his primary offer works:
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"Have you thought about where you could cut some of that? Or find a way to outsource it so you don't do it all yourself?"
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The product in question is his podcast audits, where he spends 5-10 hours listening through a client's content and poring over their show and business collateral...
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Then, organizes his notes and records a video audit that usually clocks in between 2-3 hours in length.
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In short, the audits are exhaustive.
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But there's a specific reason he does them this way.
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Free workshop

March Topic: Leading Yourself and Your Team

Mar 19, 12 pm ET

When there's so much to do, how do you organize yourself - and your team - towards action?

​In today's class, we'll break down how to lead yourself and your team with alignment to your goals.

  • ​Distinguishing between ideas, projects, areas, and tasks
  • ​How to prioritize what's most impactful
  • ​Strategies for delegation, and how that changes between projects, areas, and tasks
  • ​Keeping aligned with yourself and your team

Community and Reads

​25 Min Insight-Swap: Demand Gen for Mid-Sized Business with Rebeca Arango​

I'm Rebeca, expert copywriter and content strategist. I work with $1-$50M revenue businesses in education, wellness, and b2b services, and partner with the agencies and consultants who serve them.

If you're a CMO, CEO, agency strategist or consultant in my space, let's meet.

I've specialized in conversion copywriting and ghostwriting for over a decade, with a focus on compassionate persuasion techniques. My clients see significant increases in their content performance while approving their marketing faster than ever.

As I consider what the market needs in 2025, I'd love your input. In exchange, I'll offer my expert perspective on your current messaging, website, brand assets, or content.

​No one’s coming to save you: A designer’s unfiltered take on surviving a brutal market​

I won’t deny luck exists. But I hate when people say “Oh, you were just in the right place at the right time,” because that minimises the work it takes to put yourself in the right place at the right time.
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For example, my most recent job? It happened because you introduced me to someone, that someone introduced me to someone else. But those introductions also happened because I’ve spent years making sure people can find me, that my work speaks for itself, and that I’m always paying attention to where the market is moving.
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A lot of folks are out here waiting for someone to tap them on the shoulder and say, “Hey, we have a job for you!” That’s not how it works. You have to make yourself obvious.

If you're not already following Allison Davis and you want to sell five-, six- and seven-figure deals at into organizations... just do it. Sign up for her monthly roundtables and get a dose of warm but necessary sales insights.

(I learned a new term this month: FOMU - Fear of Messing Up!).

Jessica Lackey

START INVESTING IN YOUR BUSINESS FOUNDATIONS

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  • ​Deeper Business Membership: A low-lift but high-impact membership to learn and implement the core Deeper Foundations frameworks, and build connections with others doing the same.
  • ​Deeper Foundations: The foundational curriculum, coaching, and community if you're ready to stop throwing tactics at the wall and start building real, sustainable foundations. March cohort is enrolling now.
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Jessica Lackey | Harvard MBA turned Small Business Strategist

Build your business - and your business-building intuition with foundational frameworks and practical application.

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