Famous Entrepreneurs Who Failed Before They Succeeded

The big meeting is finally here. You practiced the pitch again on the drive over and told yourself this one is different.

Twenty minutes later, you’re back in the parking garage with a polite pass and a stomach that won’t settle. That sour feeling is part of the game. It comes with building something you believe in.

Melanie Perkins, Frederick W. Smith and Arianna Huffington hit that wall. Before their names became synonymous with success, each founder came dangerously close to watching the whole thing fall apart.

Discover what these entrepreneurs did to fix what needed fixing, found another route and made the next call. 

SBA Proposes Overhaul to Simplify Small Business Classification

The U.S. Small Business Administration (SBA) proposed a comprehensive overhaul of its small business size standards, modernizing how the federal government defines and classifies small businesses across the United States. Published in a proposed rule, the new standards according only to SBA, would simplify industry categorization and raise applicable size thresholds, allowing small but rapidly growing firms to continue qualifying and adding over 110,000 firms to the 36 million small businesses in America.  

Small businesses, the economic engine of America's growth, are starting and expanding at record rates.  Rule change or no rule change, they will continue to drive America's economy. 

Is Your Business Built to Survive?

Every business plans for growth. But how many are built to survive? If your business lost everything tomorrow, what would it need to continue to operate?  And how can you maintain momentum when disruption strikes?

In this episode of Take on Tomorrow, PwC UK explains why organizations need to identify their ‘minimum viable company’ – the people, systems, and services that absolutely must keep running when disruption hits – and why a crisis plan alone may no longer be enough. 

Listen to the podcast or read the transcription here.

Fantastico! Inside the 23rd Annual WPO Chicago Summit (9/10/26)

©2026 Laurel J. Delaney.  All rights reserved.

What an amazing program at our 23rd Annual Women Presidents Organization Chicago Summit (9/10/26).  Fantastico!

Thank you to our Steering Committee: Nida Khan, Founder & President, Arya Consulting Partners (Chicago I member), Lauren M. Loew, Partner, Foley & Lardner LLP (Chicago II member), Ellen M. Wheeler, Partner, Foley & Lardner LLP (Chicago I member), Laurel Delaney, President, Women Entrepreneurs Grow Global (WPO Chicago Chapter Chair) for their leadership; to the Foley & Lardner LLP support team for their outstanding work behind the scenes; to Andrew Sykes, CEO of Habits at Work for a compelling talk on "Your Trust Advantage;" and to all who attended for your engagement throughout the day.

The photo collage above captures the moment!  

More about the program here:

https://womenpresidentsorganizationchicago.blogspot.com/2026/08/wpo-chicago-summit-910-your-trust.html

Recharge on Labor Day

Labor Day may mark the unofficial end of summer, but it’s far more than just an extra day off. Born from the labor movement of the late 19th century, the holiday was created to honor the hard work and dedication of America’s workforce – that includes all WPO members. For the 21st century, it’s a built-in reminder that pausing to recharge isn’t indulgent, it’s essential. 

This Labor Day weekend, instead of simply letting the hours slip away, why not make the most of your well-earned time off?

Find some inspiration here. 

23rd Annual WPO Chicago Summit With Andrew Sykes (9/10/26)

©2026 Women Presidents Organization Chicago.  All rights reserved.

Join us for our 23rd Annual WPO Chicago Summit on Thursday, September 10 in Chicago at 1:30 PM CT.  Our keynote and workshop leader is Andrew Sykes, CEO, Habits at Work and he will speak on "Your Trust Advantage:  How To Be the Most Trustworthy Leader in Every Room."

Learn more here.  For members and sponsors only.

WPO Chicago Summit 9/10: Your Trust Advantage with Andrew Sykes

©2026 WPO Chicago.  All rights reserved.

Join us for our 23rd Annual WPO Chicago Summit on Thursday, September 10 in Chicago at 1:30 PM CT.  Our keynote and workshop leader is Andrew Sykes, CEO, Habits at Work and he will speak on "Your Trust Advantage:  How To Be the Most Trustworthy Leader in Every Room."

As leaders, we have trust issues, including many that we might not know about! In this session, Andrew will highlight these trust issues, understand how others assess our trustworthiness and explore some of the myths about trust, replacing them with not only research-based truths, but practical ways to become the most Trustworthy person (and leader) you know!

WPO Chicago Steering Committee

• Nida Khan, Founder & President, Arya Consulting Partners (Chicago I member)
• Lauren M. Loew, Partner, Foley & Lardner LLP (Chicago II member)
• Ellen M. Wheeler, Partner, Foley & Lardner LLP (Chicago I member)
• Laurel Delaney, President, Women Entrepreneurs Grow Global (WPO Chicago Chapter Chair)

Hosted by:  Foley & Lardner.

Interested in attending?  If you pre-qualify for WPO Chicago membership and would like to attend, kindly email Laurel Delaney (noted in the agenda above), WPO Chicago Chapter Chair.

This event is for members and WPO sponsors only.

The Effective Feedback Structure

Giving effective feedback isn't an innate talent reserved for a select few. According to Harvard Business School Professor Joseph Fuller in the online course Management Essentials, it’s a skill that can be built through deliberate practice.

Whether you're giving or receiving feedback, these five practical exercises can help you turn vague comments into clear, constructive conversations. 

What Actually Happened When OpenAI's AI Went Rogue

During an internal cybersecurity test, an AI agent powered by an experimental OpenAI model was tasked with a benchmark exercise. Instead of staying inside its sandbox, the agent reasoned its way out, discovered a previously unknown vulnerability and used stolen credentials to reach Hugging Face’s production servers, pulling out the information it needed to complete its assigned task.

So what does this mean for you?

The model wasn’t hijacked by an outside attacker. It made an autonomous decision to break a boundary because that boundary was in the way of finishing its job efficiently – similar to your tireless workers.

That is precisely the behavior every AI agent you deploy is optimized to exhibit, just usually with lower stakes and better-defined limits.

Learn more about how this fallout gap is impossible to ignore and what actually happened when OpenAI's AI went rogue.

Leverage the Arts and Storytelling for Greater Data Impact

Most of you reading this blog have worked in a company setting.  You have likely sat in a room where someone presents a slide deck loaded with charts, numbers, and bullet points. The presenter seems prepared, and everyone nods politely. But do you really remember what is shared, and do you really care about the data or act on it? Often, that answer is no.

How do we turn that around so that you find yourself remembering, caring about, and acting on what you learned?

Discover why storytelling is such a powerful driver of action, and why facts alone rarely move people.

AI Isn't a Substitute For Human Skills

As Michael Fenlon, Executive Director of Harvard Online and former Chief People Officer of PwC, puts it, in an age of AI, “nobody in an organization is paid to be average.” Technical skills are now table stakes; what differentiates individuals and organizations is the ability to turn AI capability into business impact.

AI can generate options; humans still must decide what problems are worth solving. Companies need leadership – not automation.

Kendra Scott Eyes Global Expansion

All businesses – whether service or product-based – need to consider taking their business global.  It's a good growth method.

Take Kendra Scott.  She recently named Adrienne Gernand the company's first chief business officer.

In her new role, Gernand will be responsible for broadening the scope of the Kendra Scott brand through category growth and global expansion. 

Gernand comes with experience helping scale such retail brands as Old Navy, Gap, Banana Republic, Athleta and The Children’s Place. She has worked on new market entry models, the optimization of real estate portfolios and the formation of strategic partnerships.

Learn more how Gernand will identify high potential global growth opportunities for Kendra Scott.

The Hidden Tax On Every Interrupted Thought

What's the rarest skill in the modern economy?  Attention span.  I may have lost you already.

There is a version of productivity that looks like motion but produces very little. You know it when you see it – the day full of switching, responding, reacting – and you know it even better at 5 p.m. when you can’t quite name what you actually accomplished. It felt busy. It wasn’t deep.

What you were practicing, without choosing to, is the dominant cognitive mode of the modern era. And what you were not practicing is the discipline of one thing.

Find out what the hidden tax is on every interrupted thought.

Oh, and keep this in mind:  What the biographical record of high-achievers tends to reveal, stripped of legend, is not supernatural talent but an almost stubborn commitment to staying with a single problem long enough for it to yield.  To achieve that, you must not just work differently, but think differently. 

1.9% Isn't a Ceiling. It's a Gap.

More women are planning to start businesses this year than ever before. According to an “Entrepreneurship in 2026” survey by QuickBooks, one in four women plan to launch a new business this year. Another 58 percent say they would consider it. 

Only 1.9% of women-owned businesses ever reach $1 million in annual revenue. Not because women aren’t capable, but because the system – and often our own beliefs about money – have held us back.

Imagine if 10% of women-owned businesses hit $1M.  The Women Presidents Organization (WPO) would be fortunate to serve them all!  

That 1.9% isn't a ceiling. It's a gap – and gaps are where organizations like WPO do their best work. Every woman who joins a peer advisory group, finds a mentor, or simply decides her business deserves to be a $1M business is closing that gap, one decision at a time.

The women starting businesses this year don't need permission. They need community, capital, and a peer group that expects them to think bigger. That's what WPO and WPO Chicago is here for.

So here's the real question: What would it take for your business to be one of the 10%?

A Simple Five-Question Audit Before Scaling with AI

Most leaders assume AI success comes down to technology. After helping organizations navigate digital transformation for years, Matt Domo can tell you that is rarely the deciding factor. He has worked with companies that invested millions in data platforms, machine learning models and AI tools only to see minimal business impact.

Before he helps any company scale AI, he runs a simple five-question audit.  The first question is always the most important because everything else depends on the answer.

Learn more about the five-question audit.

Technology may power transformation. Leadership determines whether transformation actually happens.

Don't Guess How You Are Perceived

Most leaders spend a lot of time guessing how they are perceived. Some don't even care.

For example, I was on a pretty contentious Zoom call recently with two business women and when I got off, one of the women later said to me, "she's not self-aware," and sadly I knew exactly what she meant.

According to coaching and leadership guru Marshall Goldsmith, he says, "The truth is simple. You cannot read your own label. You are too close to the problem."

If you want to know what is written on your jar, you have to do the one thing that many leaders avoid doing:  Ask.

Goldsmith says that is the foundation for real growth.

Unicorn Female Founders

Ilya Strebulaev, Professor at Stanford GSB says, "6.5% of US unicorn founders are women. Out of 4,545."  He goes on to say.

Companies with at least one female founder have a 35% lower probability of reaching unicorn status than all-male teams — that's the actual regression result, controlling for the VC-backed comparison group.  When I did the same analysis several years ago, the probability was 40%. So it is moving, but very slowly. 

Read his entire LinkedIn post here. 

Female Founders Are On the Rise

Female founders are on the rise. According to a 2025 Gusto New Business Formation Report, 49% of startups in 2024 were women-led. It’s a milestone to celebrate, but the numbers don’t tell the whole story about the challenges faced by female founders.

For example, women are less likely than men to get backing for their companies. As an academic piece from the Journal of Small Business Strategy notes, the reasons are complicated: limited access to investors, assumptions of being higher credit risks, and a generally biased perception. These barriers mean more women may have to take the bootstrapping route to launch their ideas into the marketplace. 

To their credit, plenty of female entrepreneurs overcome initial funding difficulties and wind up running successful businesses.  WPO members are a great example.

Five Pieces of Advice From Successful Women Business Owners

Women business leaders are blazing a trail to success. Along the way, these women – many are Women Presidents Organization members – are demonstrating powerful tactics and traits essential to growing a sustainable business.

Let’s look at five pieces of advice from women who have risen to the top.

Four Lessons On Building a $1.75 Trillion Company

On May 20, 2026, SpaceX filed its S-1 with the Securities and Exchange Commission, the formal opening move toward what is projected to become the largest IPO in history, targeting a valuation of up to $1.75 trillion. 

Most headlines focused on the rockets, the Mars obsession and Elon Musk’s ironclad voting control. But if you’re a founder (which many WPO members are), an executive scaling a team or anyone building something intended to last, this 270-page document is a startup strategy masterclass hiding in plain sight.

Here's what SpaceX can teach you.