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Taylor Sloane and the art of closing the chat window
The HelpDocs co-founder likes getting the details right, down to the dissolved solids in a cup of coffee. Building a software company has also taught them when to stop, listen, and change the recipe.
Wolfram built the engine. AI brought the questions.
For nearly four decades, Wolfram has been teaching computers to calculate, model and explain. The chatbot boom gave its old ambition a new customer: AI itself.
miniOrange makes the old world log in.
The hardest part of modern security is often the software nobody can replace. miniOrange has built a business around getting that software to cooperate.
CodeVyasa makes the boring bits work.
A software business can look healthy while its testing, cloud bills, and data quietly get out of hand. CodeVyasa has built its pitch around fixing those problems - and carrying the work through to production.
360 Degree Cloud and the art of making Salesforce earn its keep
A Salesforce partner built a business on keeping work inside the CRM. Its most revealing case study asks whether some of that work belongs somewhere else.
Hampton puts founders in the same room.
A private network built on small groups discovered the limits of the video call. Its next chapter asks successful founders to do something surprisingly difficult: show up.
Audrey McLoghlin and the strange power of one good shirt
She built Frank & Eileen around a single silhouette and kept the company in her own hands. Now Audrey McLoghlin wants more women to have the knowledge and freedom to build businesses of their own.
Yaakov Karda and the business hiding in the help desk
His custom-jeans company closed. The customer-service experience survived. With Chatra, Yaakov Karda turned an everyday skill into a business people already knew they needed.
Social Strata (Crowdstack)
For more than two decades, a husband-and-wife team in Charleston has quietly powered online communities for brands that outgrew Facebook Groups - and never took a dime of venture money.
Mediavine turned the ad problem into the business.
It built advertising tools to pay for its own websites. Then the neighbors came knocking. Today, Mediavine helps more than 20,000 publishers turn attention into income.
The Pragmatic Engineer sells a better question
Gergely Orosz built a reader-funded publication around the details tech headlines leave out. Its real product is knowing what to ask before you copy another company’s engineering playbook.
Exit Five and the $100,000 exit
Dave Gerhardt lost customers to build a better home for B2B marketers. The bet reveals what people will pay for when advice is everywhere and useful company is harder to find.
Entrepreneurs on Fire made every day a business.
John Lee Dumas filled the silence between business podcasts. Then he and Kate Erickson turned a daily interview habit into courses, journals, and a company willing to show its arithmetic.
Foundr Podcast: Give the interview away.
Nathan Chan worried a free podcast would eat his magazine. A six-month bet helped turn the same conversations into the front door of an education business.
Mars Men built a repeat order before it raised a round
A testosterone-support subscription became a business with a reported $100 million revenue run rate. Now Mars Men is taking its formula for repeat purchases into retail and cognitive performance.
CAKE.com built the tools it wanted to stop paying for
Eight failed products preceded Clockify. Then CAKE.com turned its own office irritations into a three-app business - and made the price part of the product.
Tally built a business by giving the forms away
A hotel startup lost its customers. Its founders kept the paperwork - and turned a familiar irritation into a customer-funded form builder with a very generous front door.
TechSmith built a business on “Let me show you”
A screenshot can end an email chain. A tutorial can outlive a meeting. TechSmith has spent decades turning those small acts of explanation into software people pay for.
Cloudinary built a business on the image nobody wants to resize
Every beautiful website has an unglamorous back room. Cloudinary turned that room into a service, then grew to $100 million in annual recurring revenue before Blackstone bought a stake.
SMS-Magic learned that the message needs a memory
Now called Conversive, the CRM messaging company is betting that AI can finish the conversation - provided it remembers how it started.
SMARTe and the surprisingly expensive wrong number
A bounced email looks like a small mistake. SMARTe has built a business around what happens when thousands of those small mistakes become the way a sales team works.
Awesome Motive: the free blog behind 30 million websites
Before it sold software, Awesome Motive taught people how to use it. Its journey from WordPress tutorials to a sprawling product portfolio shows what happens when the help desk becomes the product department.
Omnisend and the profitable art of showing up on time
In Omnisend’s 2025 data, automated messages produced 30% of email revenue from just 2% of sends. The company has built its business around a small merchant’s large problem: knowing when to speak.
Infragistics: When the parts became the business
A tool that once supplied 80% of revenue came under threat. Infragistics found its next business in the grids, charts, and interfaces other developers would rather buy than build.
Tax Technologies and the art of selling yesterday
Before asking a company to buy Tax Series, Tax Technologies offers to reproduce a year of its tax work. In a business devoted to calculating the future, yesterday makes a surprisingly persuasive sales pitch.
314e and the Hospital’s Unfinished Business
A new electronic health record does not retire the old records, teach the staff or tame the fax queue. 314e has built a business around the work that survives the upgrade.
ClickFunnels and the art of the next yes
A sales funnel company discovered that its own customers needed a lesson before they needed a login. That discovery still explains the software, the spectacle, and the subscription.
The Speaker Four Friends Built Because Everything Else Broke
Turtlebox Audio spent more than a decade turning a Buffalo Bayou garage project into one of America's fastest-growing private companies - by building a speaker loud and tough enough to outlast the water, the drops, and the duck blind.
The Doctor Who Sewed Her Way Out of a Sleepless Night
A family doctor could not fall back asleep after 3 a.m. patient calls. Regular headphones hurt, earbuds fell out, so she built a pillow-friendly pair - and turned a kitchen-table fix into a global sleep-tech brand.
The Agency That Sent 1,000 Micro-Influencers Into Battle and Never Took a Dime of Venture Money
Mae Karwowski bootstrapped Obviously out of a Lower East Side apartment, turned down a $25 million offer, and sold to the world's biggest ad holding company. The trick was treating influencers like a data problem, not a popularity contest.