I’m 45. After 25 years building startups, selling a company for near 9 figures, and advising dozens of founders, I’ve made just about every career mistake in the book. Here are 20 pieces of brutally honest career advice (I wish someone had told me earlier):

https://t.co/hHh10eBB6O

DTC brands - let's talk margins. People worry about "stepping over dollars to pick up pennies", but they forget it's not mutually exclusive. You can bend over to pick up a $5 and grab a $1 at the same time! Found Revenue -- what is it? 1. It's a killer post-purchase upsell. 2.

Yesterday, I was reminded of a powerful lesson in integrity. Taking inspiration from content is par for the course and simply a part of the game -- copying other people's words/content is a step too far. Background: A few months back - I lifted a hook and the outline of a post

In June, @useonward grew 10.5% month-over-month to a $13m run-rate, profitably and completely bootstrapped. Driven by our highest new logo month ever! WHAT'S WORKING: - Made major upgrades to tech + ux + product planning processes during our latest offsite. - Took the week to

Just back from @useonward's 7th offsite - here are 7 key improvements we made to make this one our most effective yet. [+ Free Notion Template] Over the last 2+ years and conducting 7 offsites, I've learned a thing or two about what works and what doesn't. Here's where we

https://t.co/VKWSTf1CUj

5-bullet recap from The Seed Money Pod w/ Jayla Siciliano where we covered why Seed-strapping is the hottest trend in VC right now. 👇 1. I've been preaching Seed-Strapping for well over a decade and the premise is not only that it keeps the founder in control, but that it

We just wrapped an incredible offsite in Jackson Hole with the Onward team And what came out of it surprised me... ~~ These moments away from the daily grind are where real culture is built. Not just through strategy sessions or growth reviews—but through shared experiences,

Steve Jobs: “Don’t be a career.”

Paul Graham on why you should work on your own projects:

P.S. If you enjoyed this post, you'd like my newsletter. I share hard-earned lessons from scaling a startup to 9-figures & how I'm building a new one all over again. Try it free here:

Most brands chase revenue. The best brands optimize the right metrics. Track these 10 KPIs and watch your profit, retention, and scale transform overnight. Follow @jnpayne for deep dives on DTC, SaaS, and investing.

10. % of Revenue from Returning Customers A healthy DTC brand makes 40%+ of revenue from repeat buyers. If you’re below that, focus on LTV levers: • VIP memberships • Personalized email/SMS offers • Post-purchase nurture flows

Turn one-time buyers into multi-SKU customers with: • Bundles • Exclusive add-ons • Subscription perks A strong SKU mix = long-term stability.

9. SKU Concentration Risk If 80%+ of your revenue comes from one product, you’re vulnerable. Great brands expand without overextending.

The fix? • SEO & content marketing • Affiliate & referral programs • Retention tactics (VIP, loyalty, subscriptions) If you’re only scaling with paid ads, you’re building on shaky ground.

8. Organic vs. Paid Revenue Ratio If 60%+ of your sales come from paid ads, you’re in trouble. Brands with real staying power win on organic channels.

7. Refund & Return Rate A high return rate = a CAC multiplier. Fix it by: • Charging for returns (but offering free exchanges) • Clearer product descriptions & sizing charts • Post-purchase emails on how to use the product

If you're below that: • Increase prices (test 10% bumps) • Reduce discounting, do Cashback instead (@ Onward) • Negotiate better supplier terms (carrier rates, 3pl, etc) Without margin, you don’t have a real business.

6. Gross Margin per Order (The Scaling Checkpoint) AOV is meaningless if your margins are razor-thin. At scale, 40%+ gross margins keep you profitable.