What do you do when your business is struggling, and you're not sure what to try next?
For marketing powerhouse Jay Schwedelson, the answer has been surprisingly simple: keep showing up, keep testing, and be yourself.
Jay shares how he grew up in a family direct-mail business, built an agency combining direct mail, email and digital marketing, nearly lost the business during COVID—and then completely changed his approach to marketing by becoming more authentic and visible.
We talk about why consistency beats perfection, why small businesses shouldn't expect every marketing dollar to have a straight line back to revenue, the power of human content, why the owner of a small business may need to become the brand's biggest megaphone, and the $30-a-week marketing tactic Jay believes small businesses are overlooking.
And, of course, we get into Jay's bestselling book, Stupider People Have Done It, and the advice from his grandfather that inspired it all.
WHAT YOU'LL LEARN
- Why consistency can beat sophistication in marketing
- How COVID forced Jay to stop trying to play the industry's game and start being himself
- Why human, behind-the-scenes content can make your business more relatable
- Why the first version of almost anything you do is probably going to be bad—and why that's OK
- How to think about the 95:5 marketing reality and staying visible before customers are ready to buy
- Why marketing attribution isn't always as clean as “I spent $1, I made $X”
- Why small-business owners may need to become the megaphone for their own business
- Jay's micro-boosting strategy for putting a small amount of paid media behind social content
- Why regret can be worse than failure
- How Jay's grandfather inspired the title and philosophy behind Stupider People Have Done It
⏱️ EPISODE TIMESTAMPS
01:11 — From Internet Advertising to Direct Mail & Digital
03:04 — The COVID Crisis That Changed Everything
03:58 — Growing Up in a Family Direct Mail Business
07:05 — The Entrepreneurial Mindset: “Just Friggin’ Try It”
09:51 — Jay’s Early Hiring Mistakes & Learning by Doing
13:16 — When the Business Grows With You
14:43 — Why Being Yourself Changed Jay’s Business
17:44 — Being Human Is the Secret Sauce
21:23 — The Marketing North Star: Consistency
24:44 — Why You Have to Keep Showing Up
25:14 — The 95:5 Reality & Why Consistency Wins
26:32 — The Problem With Marketing Attribution
29:14 — The Story Behind “Stupider People Have Done It”
34:16 — Why Small Businesses Need a Human Face
35:16 — Make Yourself the Megaphone
42:35 — Why Now Is a Great Time to Start a Small Business
44:37 — The Reality of Stress, Anxiety & Entrepreneurship
46:17 — Jay’s $30-a-Week “Micro-Boosting” Strategy
48:47 — What’s Next: AI, Events & More Content
49:37 — The Future of Direct Mail & Small Business Marketing
52:30 — Marketing Is an Investment, Not an Expense
54:01 — “I Can. I Will.”
💬 THE BIG IDEAS
1. Consistency Beats Perfection
This may be the biggest takeaway of the entire episode.
Jay says he isn't the smartest person in the room. His answer to that problem wasn't to become smarter than everyone else—it was to become more consistent than everyone else.
He talks about continuing to post, email, podcast and create content even when he's wondering whether any particular activity is generating revenue.
“Consistency will beat out smartness every day of the week."
2. Stop Trying to Sound Like Everyone Else
He realized that he had spent years trying to communicate, present and market himself the way everyone else in his industry did. Then he started experimenting with simply being himself.
The content that felt most natural to him performed better—and that became a turning point in his business.
His lesson:
Your personality can be a competitive advantage.
3. Human Is the New Differentiator
Jay argues that businesses have an opportunity to show the humans behind the brand through lo-fi, behind-the-scenes content: manufacturing, service calls, day-to-day operations, conversations and the things that make the business real.
For a small business, this is particularly powerful because customers aren't necessarily choosing you because you're the biggest.
They're choosing you because they know you, trust you and like the experience of dealing with you.
📬 THE MARKETING LESSON: STAY VISIBLE
If 95% of folks aren't ready to buy now, it means you need to stay visible until the moment someone is ready.
He uses direct mail as an example: a postcard may arrive today, sit on a desk, and do nothing. Then another arrives later. Eventually, the customer needs the service—and suddenly the company they've been seeing repeatedly is the company they remember.
Consistency is how you win.
And Jay makes another important point: not every marketing interaction will have a perfectly measurable attribution trail.
A customer may see a social post, receive an email, get a postcard, hear about you from a friend, visit your website and then contact you. Trying to assign the entire purchase to one marketing activity can cause businesses to abandon channels that are contributing to the overall result.
📖 THE STORY BEHIND STUPIDER PEOPLE HAVE DONE IT
Early in Jay's career, he was struggling. He didn't think he was capable of building a successful business.
His grandfather came into his office, saw Jay sitting there with his head in his hands, and gave him some unforgettable advice:
“Stupider people than you have been able to do it.”
Instead of discouraging him, Jay found it incredibly motivating.
His grandfather had another message, too:
The phone isn't going to ring by itself.
You've got to pick it up and do something.
That became the philosophy behind Jay's book—a combination of motivation, life lessons, marketing tactics and humor. Jay says the book has generated more than $130,000 in donations to the V Foundation for Cancer Research.
💡 THE BIG BUSINESS LESSON
Don't confuse “I can't see the result yet” with “it's not working.”
That's the thread running through so much of Jay's story.
He didn't know his first Internet advertising company would become an agency.
He didn't know the virtual conference he launched during COVID would become a media business.
He didn't know his more authentic social content would change the trajectory of his business.
He didn't know which individual marketing activity would produce the next client.
He kept trying.
He kept showing up.
He kept marketing.
And he kept becoming better at being Jay.
That's a pretty damn good lesson for a small-business owner.
👤 ABOUT JAY SCHWEDELSON
Jay Schwedelson is a marketing entrepreneur, agency owner, media entrepreneur and advocate for small businesses.
He is the founder of Outcome Media, a demand-generation agency working across B2B, consumer and nonprofit marketing, and has built a media business around large-scale virtual events covering marketing, email, direct mail, AI and more.
Jay grew up around his family's direct-mail business and eventually combined Internet advertising, email and direct mail into an agency that grew to approximately 100 employees. During COVID, he began building a much larger personal presence through social media and virtual events, creating an entirely new dimension of his business.
He is also the author of Stupider People Have Done It, a book inspired by his grandfather's advice during a difficult point in Jay's entrepreneurial journey.
Need Help Growing Your Business?
PostcardMania helps small businesses grow through education, marketing, and technology.
From direct mail to digital marketing and integrated campaigns, learn how we can help you reach more customers.
Visit: https://www.postcardmania.com
Looking for more Marketing Education?
PostcardMania has ongoing webinars to help you really learn about marketing - no fluff, just real, practical help so you can better understand how to best grow through marketing that actually works.
Visit: https://www.postcardmania.com/webinars/
Let's Connect!
Have a small business story, lesson, or experience you'd like to share? Be a guest on our show!
Email: [email protected]
