Hello Reader!

Imagine this.

It's 2022. Your business is doing GREAT. You're making multiple 6-figures. You work 20 hours a week. You're working with a small, smart team.

You've also started a newsletter, and it's gaining traction. People are subscribing, open rates are high, and relevant brands are sponsoring it. Yay!

You are also thinking about starting a podcast with one of your freelance buddies. You head to Mexico to record, and it ends up being a hilarious joy.

You've also created a business that allows you enough income and time to do what you care about. You travel with your family. You take a humanitarian trip to Ukraine to translate for a group of lawyers. You're doing great.

It's still 2022, and you agree to go on a podcast with a Big Deal In The Industry. The plan is for you to ask Big Deal 5 questions about HIS business. Cool. No problem.

You prep your questions and hop on the podcast.

The podcast starts, and the host goes rogue. You are not asking Big Deal questions. He's asking you questions about your business.

You're thrown off a bit because he clearly has no idea who you are and knows nothing about your business. You play along.

He starts consulting you.

He belittles you & your business.

He asks you why anyone would care about your newsletter.

He tells you your ideas are gimmicky.

He offers nothing helpful.

Ultimately, Big Deal is a jerk to you.

You leave the podcast feeling bad about the business you've built and your ideas.

After all, he's Mr. Big Deal.

You wonder: maybe this business I've built IS a failure. Perhaps my ideas ARE gimmicky. Maybe no one wants to read my newsletter because I'm not The Freelancer He Said You Had To Be To Be Worthy Of An Audience (he used an actual name).

It shakes you.

Fast forward 3 years.

You still have a thriving business and newsletter. He's still Big Deal.

You sign up for a conference. Big Deal is a speaker.

You attend because you respect the conference hosts.

He starts his speech. It's cute. He's handsome and a smooth talker—a good orator.

He gets vulnerable. He pulls up a slide from 2022. His business wasn’t doing great. Things were not looking good. He didn't know what he was going to do. Big Deal had to start from scratch.

Well, math's not my strong suit, but some things weren't adding up.

Big Deal's business was failing back then.

Yours was (and still is) absolutely thriving.

You let what he told you bother you for 3 years. You second-guessed yourself. Every so often, Big Deal's voice crept up, critiquing a new idea of yours.

And then, in 2025, it was gone.

The lessons?

Maybe the Big Deals in the Industry aren't actually that big of a deal. Maybe when someone belittles you, they're saying more about themselves and their current state than they are about you and yours.

And other industry friends you love may still put him on the big stage and pass him the microphone.

But you don't need to give him the mic. And if he takes it, you don't have to listen.

Thanks for reading,

Ashley R. Cummings

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Expert Interview | Sumeet Ganju

This week, we’re featuring Sumeet Ganju, a registered investment advisor and founder of InverseWealth.

InverseWealth is a modern wealth management firm helping freelancers, professionals, and small business owners build lasting wealth.

After years in Silicon Valley’s executive ranks, Sumeet started InverseWealth to make powerful financial planning & investing strategies accessible to everyone, and not just the ultra-wealthy.

1. What’s the one way freelancers can turn inconsistent income into consistent wealth?

By having a solid investment & cash-flow plan. Too often, freelancers have too much money lying around in checking accounts or forgotten retirement accounts that's not generating any returns. Or they invest erratically in stocks based on what their friends recommend, or what they see in the news. Most of my clients were only investing in the S&P 500 via index funds before they hired us. The S&P 500 is simply not diversified enough and can expose you to serious market risk at the same time as the economy and your freelance income weakens. Having a balanced investment strategy that reduces risk while generating returns is essential for building long-term wealth, especially when your income is not consistent or guaranteed. It takes years to build wealth and only a short time to lose it.

2. How can you help me save more on taxes without spending hours tracking every tiny expense?

There are so many strategies that can help freelancers and business owners save taxes. For example, just making the right business entity selection (S-Corp vs LLC vs sole-proprietorship), can unlock thousands of dollars in tax-savings. Each business entity comes with it's own compliance requirements, so its critical to know the pros-cons before making a decision. Similarly choosing the right type of retirement accounts (SEP IRA vs Solo 401k) or choosing tax-efficient investment strategies (such as direct indexing and tax-loss harvesting), can generating big savings when compounded over just a few years. Remember, Turbo Tax (& most CPAs) only file your tax returns - they don't specialize in proactive tax planning strategies.

3. What's the most common financial gap that you've seen?

Not having enough protection. It's one of those things that you don't really think about, until it's too late. While most people are aware of health insurance and life insurance, they tend to overlook disability and umbrella insurance. Salaried employees typically get short-term and long-term disability insurance from their employer. As a freelancer, you need to make sure you have some income replacement coverage in case something goes wrong and you are unable to work. The umbrella insurance protects your assets in case you are ever faced with a liability claim. It's generally quite inexpensive for the level of protection it provides. These are protections that every freelancer should seriously consider.

Must-Read Industry Content

Think smarter, faster: Each week, I share the articles that are shaping where content marketing is going, so you don’t have to dig.

1/ You Have No Idea How Screwed OpenAI Actually Is (This is completely bonkers)

2/ Your next clients might be on G2. Here's how to find them

3/ 5 Things Killing Your Writing Portfolio & Your Credibility

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