Thirty ventures in. Still shipping.

STEVE
TAPLIN

CEO, Sonatafy Technology · Author, Fail Hard Win Big · Forbes Technology Council

What thirty ventures taught me about leadership, building companies, and shipping software that actually works.

Portrait of Steve Taplin
30
Companies
20
Failed
10
Succeeded
30+ Companies Built20 Failures10 SuccessesAmazon Bestselling Author248+ Forbes & Entrepreneur Articles180+ Podcast EpisodesCEO Sonatafy TechnologyForbes Technology Council Member30+ Companies Built20 Failures10 SuccessesAmazon Bestselling Author248+ Forbes & Entrepreneur Articles180+ Podcast EpisodesCEO Sonatafy TechnologyForbes Technology Council Member

The Story

I've started thirty companies. Twenty failed. The ten that worked taught me what no MBA can.

If your team feels busy but ships nothing, you are not alone. This is what thirty attempts taught me about the difference.

Tech CEO. Serial Entrepreneur. Speaker. Author.

TThirty companies built. Twenty failed. Ten succeeded. Every one of them a lesson in leadership, resilience, and what separates the founders who ship from the ones who stall. Steve is the CEO of Sonatafy Technology, where he and his team solve the problem most software organizations refuse to name: the gap between engineering capacity and engineering outcomes.

As a Forbes Technology Council member with 248+ published articles, host of Software Leaders Uncensored (180+ episodes), and author of Fail Hard, Win Big, Steve has spent two decades inside the machinery of software delivery, AI adoption, and the leadership decisions that determine whether either one works.

He writes about leadership and entrepreneurship the way he has lived them. Honest, expensive, and earned.

The Newsletter

THE TECH
DILEMMA

A weekly newsletter on leadership, entrepreneurship, and what thirty ventures keep teaching about building companies that ship.

No fluff. No recycled thought leadership. Just the patterns I see across founders, CEOs, and engineering leaders every week.

Unsubscribe anytime · No spam

Read a recent issue

In The Press

RECENT PUBLISHED INSIGHTS

See all 248+ articles

Books

ON THE SHELF

Fail Hard, Win Big book cover
Bestseller

Fail Hard, Win Big

The 30/20/10 journey. Brutal truths, earned the hard way.

The Backlog Illusion book cover
Just Released

The Backlog Illusion

Why your roadmap feels productive — and ships nothing.

GO DEEPER

01

Sonatafy Technology

sonatafy.com

Software delivery acceleration

Managed Delivery PODs that close the gap between roadmap ambition and what actually ships. A US principal engineer paired with 2 to 4 senior LATAM engineers, US time-zone aligned, owning end-to-end delivery outcomes.

Founded 2020 · Engineering team since 2005 · Nearshore

02

Software Leaders Uncensored

youtube.com/@SoftwareLeadersUncensored

180+ episodes. Candid conversations.

Unfiltered interviews with CTOs, VPs of Engineering, and founders on what actually breaks inside high-growth software orgs — hiring, AI adoption, scaling pains, and the decisions leaders wish they could undo.

180+ episodes · Weekly · Watch on YouTube

03

Speaking & Leadership

bookstevetaplin.com

Book Steve for keynotes and workshops

Keynotes, fireside chats, and executive workshops on leadership, entrepreneurship, and the operating patterns behind thirty ventures. Tailored for tech conferences, leadership offsites, founder retreats, and board sessions.

“Steve delivers sharp, relevant insights that resonate with technology leaders.”
— John Mann, CTO of Obsess

Keynotes · Workshops · Advisory · Founder Retreats

04

LinkedIn

linkedin.com/in/stevetaplin

Connect with Steve

Daily commentary on software delivery, AI in the enterprise, and what the trenches keep teaching. Open to thoughtful connections — founders, engineering leaders, investors, and operators welcome.

50K+ network · Daily posts · DMs open

05

Free Resources

Three resources

For event organizers and founders

Three pieces of ready-to-use material: the Speaker One-Sheet for event organizers researching Steve for a keynote, the Fail Hard Win Big companion workbook with the 10 Brutal Truths every founder ignores, and The Backlog Illusion interactive workbook for engineering leaders auditing their roadmap. All free, no email gate on the one-sheet.

PDF Download · Free Workbook · Interactive Workbook · No Email Required (PDF)

Recurring Themes

WHAT KEEPS BREAKING

01

The Ownership Gap

Everyone is responsible. No one is accountable.

02

The Coordination Tax

Meetings replace decisions. Velocity dies in the calendar.

03

The Backlog Illusion

A roadmap that feels productive — and ships nothing.

04

The Founder Trap

Every founder mistakes motion for progress. The ones who survive learn the difference early.

20 failures taught more than 10 successes ever could.
— Steve Taplin