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Legend
Marin Šarić and the argument inside the algorithm
Founder · Engineer · Executive

Marin Šarić and the argument inside the algorithm

From Google’s book scanners to a robotics lab in Stockholm, Marin Šarić kept meeting the complications hidden inside simple tasks. At OptimoRoute, the next one was a working day that had to be efficient and fair.

marin-saric · optimorouteRead →
Legend
Ahmed Khairy and the Trouble With Coming Back
Founder · Executive · Engineer

Ahmed Khairy and the Trouble With Coming Back

He returned to entrepreneurship to help brands bring customers back. At Gameball, Ahmed Khairy has found that loyalty involves as much doubt, discipline and arithmetic as it does rewards.

ahmed-khairy · gameballRead →
Legend
Mitchell Harper and the business of starting again
Founder · Engineer · Executive

Mitchell Harper and the business of starting again

A PHP chat room brought Mitchell Harper and Eddie Machaalani together. Listening to merchants helped them build BigCommerce; learning when to hand over the controls shaped what Harper did next.

mitchell-harper · bigcommerceRead →
Legend
Olof Mathé and the Art of Making a Connection
Founder · Operator · Engineer

Olof Mathé and the Art of Making a Connection

Before he built a business around the inbox, Olof Mathé helped make a photo booth that needed two people. His work in software and art keeps returning to the same question: what makes a connection possible?

olof-mathe · mixmaxRead →
Legend
Joey Frasier and the Work Around the Work
Founder · Operator · Executive

Joey Frasier and the Work Around the Work

Before Worksuite’s 2023 transaction, Joey Frasier spent years connecting the unglamorous details of freelance work. His next chapter puts those operating lessons into other founders’ hands.

joey-frasier · joey-bootheRead →
Legend
Andy Powell and the business hiding in a repair bill
Founder · Operator · Executive

Andy Powell and the business hiding in a repair bill

A temperamental BMW led Andy Powell to a directory of mechanics. Proving that the directory worked led to CallRail. His career keeps turning on the same question: what is making this harder than it needs to be?

andy-powell · callrailRead →
Legend
Sidharth Kakkar and the trouble with being indispensable
Founder · Executive · Operator

Sidharth Kakkar and the trouble with being indispensable

After building Freckle, Sidharth Kakkar set out to give people back their time - at Subscript, that meant rethinking finance software and the boss’s calendar. With Woodrow, he is testing how much of the work AI can take on.

sidharth-kakkar · subscriptRead →
Legend
Tien Tzuo and the business of being chosen again
Founder · Executive · Operator

Tien Tzuo and the business of being chosen again

He helped Salesforce sell software by subscription, then built Zuora to take the idea beyond software. Along the way, Tien Tzuo discovered that a company’s founder needs an upgrade, too.

tien-tzuo · zuoraRead →
Legend
Jesse Buckingham and the art of starting over
Founder · Operator · Executive

Jesse Buckingham and the art of starting over

He helped grow a logistics software business from $2 million to more than $20 million in recurring revenue. Then Jesse Buckingham gave up the established operation to tackle the work still hiding in freight brokers’ inboxes.

jesse-buckingham · voomaRead →
Legend
Jackson Noel and the art of doing it by hand
Founder · Operator · Executive

Jackson Noel and the art of doing it by hand

Jackson Noel helped build a business that automates software onboarding. His advice to founders began with a surprisingly personal assignment: do the work yourself first.

jackson-noel · appcuesRead →
Legend
Tyler Koblasa and the trouble with explaining things
Founder · Executive · Operator

Tyler Koblasa and the trouble with explaining things

He helped turn CloudApp into a business built around showing people what you mean. Now the founder and former CEO of the company known as Zight is applying his attention to AI content, wildlife encounters, and the misunderstood shark.

tyler-koblasa · zightRead →
Legend
Timo Rein and the art of getting to no
Founder · Operator · Executive

Timo Rein and the art of getting to no

Before co-founding Pipedrive, Timo Rein sold books door to door and learned the value of a clear refusal. He carried that attention to people, time and the next useful action into a sales software company.

timo-rein · pipedriveRead →
Legend
Robert Österlund and the business of an uneventful Friday
Founder · Operator · Executive

Robert Österlund and the business of an uneventful Friday

Before Worklio, Robert Österlund took his software team on a Mediterranean cruise. His next undertaking would demand a different kind of coordination: getting payday right, under somebody else’s brand.

robert-osterlund · worklioRead →
Legend
Shailesh Kumar Davey and the value of a long innings
Founder · Engineer · Executive

Shailesh Kumar Davey and the value of a long innings

Zoho’s co-founder spent decades building the machinery behind the software. As Group CEO, he brings a patient, team-first approach to a business learning how to live with AI.

shailesh-kumar-davey · shailesh-daveyRead →
Legend
Vivien Garnes and the problem of 1,000 ties
Founder · Executive · Operator

Vivien Garnes and the problem of 1,000 ties

A necktie business left Vivien Garnes with a living room full of stock. The effort to sell it became Upfluence - and a career spent asking what influence is actually worth.

vivien-garnes · upfluenceRead →
Legend
Oleksii Kratko and the Trouble With a Cheaper Yes
Founder · Executive · Operator

Oleksii Kratko and the Trouble With a Cheaper Yes

The Snov.io founder thought a $9 option would help customers take the first step. The experiment went the other way - a useful clue to how he builds, tests and changes his mind.

oleksii-kratko · alexis-kratkoRead →
Legend
Quan Truong and the trouble with a beautiful website
Founder · Executive · Operator

Quan Truong and the trouble with a beautiful website

Quan Truong learned that giving someone a website was only the beginning. From Beeketing to ShopBase, the OpenCommerce Group co-founder has kept following the harder question: how does the merchant actually make a living?

quan-truong · quin-truongRead →
Legend
Glenn Trout and the business hiding in the paperwork
Founder · Operator · Executive

Glenn Trout and the business hiding in the paperwork

After the dot-com crash, Glenn Trout built a business around documents people still needed. His path from MSDSonline to VelocityEHS and Source Intelligence follows a stubbornly practical idea: make complicated information easier to use.

glenn-trout · velocityehsRead →
Legend
Sushil Garg and the business of the unnoticed
Founder · Executive · Operator

Sushil Garg and the business of the unnoticed

A hotel guest sees the room. Sushil Garg saw the purchasing behind it. The BirchStreet founder built a software business around the orders, invoices and small decisions that keep hospitality running.

sushil-garg · birchstreetRead →
Legend
Itzik Levy and the business of getting your day back
Founder · Executive · Engineer

Itzik Levy and the business of getting your day back

After co-founding a company acquired by Microsoft, Itzik Levy turned to businesses with no IT department. At vcita, a scheduling tool became a long-running attempt to give small business owners more time for the work they chose.

itzik-levy · vcitaRead →
Legend
Dennis van der Heijden and the art of becoming less necessary
Founder · Executive · Operator

Dennis van der Heijden and the art of becoming less necessary

A $50 WordPress plugin helped start Convert.com. A purchase request for less than $50 helped its co-founder question what a CEO was for.

dennis-van-der-heijden · convert-comRead →
Legend
Ryan Fyfe and the trouble with other people’s clocks
Founder · Operator · Executive

Ryan Fyfe and the trouble with other people’s clocks

A shift schedule once stood between Ryan Fyfe and the running track. Building Humanity taught him how much of working life depends on who gets to control the calendar.

ryan-fyfe · humanityRead →
Legend
Christian Owens and the value of the boring bits
Founder · Operator · Executive

Christian Owens and the value of the boring bits

He learned to sell software before he finished school. After building Paddle around the chores developers wanted to escape, Christian Owens is starting again with Clove - and another profession buried in paperwork.

christian-owens · paddleRead →
Legend
Jagath Wanninayake and the art of starting again
Founder · Executive · Operator

Jagath Wanninayake and the art of starting again

He sold Clarix for $40 million, co-founded a record label, and returned to software with Suvoda. His career keeps circling a practical question: how do you get people to come along?

jagath-wanninayake · suvodaRead →
Legend
Kevin Boyle and the art of making yourself useful
Founder · Engineer · Executive

Kevin Boyle and the art of making yourself useful

An Amstrad, a seven-person team, and a problem hiding inside Salesforce. How Gearset’s co-founder turned an engineer’s instinct for fixing things into the work of running a company.

kevin-boyle · gearsetRead →
Legend
Terrel Bird and the cost of being early
Founder · Executive · Operator

Terrel Bird and the cost of being early

Before internet calling became ordinary, Terrel Bird put his capital behind it - and paid for arriving early. The TCN co-founder’s story runs from an Ontario steel business to a Utah software company still changing after a quarter-century.

terrel-bird · tcnRead →
Legend
Alix de Sagazan Learned to Sell a Change of Mind
Founder · Executive · Operator

Alix de Sagazan Learned to Sell a Change of Mind

She helped turn a Paris consultancy into AB Tasty, moved to New York to build its American business, and returned to France as Wingify's revenue chief. The through line is a willingness to let experience change the plan.

alix-de-sagazan · ab-tastyRead →
Legend
Martha Bitar and the business of being understood
Founder · Executive · Operator

Martha Bitar and the business of being understood

Before Flodesk reached $36 million in annual recurring revenue, Martha Bitar was making coffee for prospective customers in her living room. Her next company asks what those same people might build for themselves.

martha-bitar · flodeskRead →
Legend
Reggie Aggarwal’s $17 million lesson in showing up
Founder · Executive · Operator

Reggie Aggarwal’s $17 million lesson in showing up

He built Cvent to get people into rooms, then nearly lost the company that did it. Reggie Aggarwal’s long second act began with fewer employees, less money, and a different idea of what deserved his attention.

reggie-aggarwal · cventRead →
Legend
Vinay Mahadik and the laptop that went home
Founder · Engineer · Executive

Vinay Mahadik and the laptop that went home

The Securly co-founder and founding CEO built a business around a school device’s life beyond the classroom. His next venture takes on another familiar problem: finding what an organization already knows.

vinay-mahadik · securlyRead →