Founder Confessions

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Being employee #5 doesn't prepare you to be a startup founder.

Goodword CEO Caroline Dell shares how she validated her idea with 100+ customer conversations, raised $5M through relationships, and uses human connection as a moat in the age of AI.

Caroline Dell, co-founder and CEO of Goodword, joins Sweta Govani for the fifth of six founder interviews in the Founder Confessions limited series.

Goodword is a networking co-pilot that helps professionals turn relationships into opportunities. It has mapped more than 8.3 million connections from people at companies like Uber, OpenAI and Airtable.

Her confession? After Bain, LOLA, and five years at Chief — where she was employee #5 and Chief of Staff and helped scale from 200 members to more than 20,000 — Caroline assumed being a founding employee was very similar to being the founder. Chief's founder laughed and said, "It's really different. You'll see."

In this episode for any startup entrepreneur building something real:

• Why being a founding employee is nothing like being the founder
• The "negative one" year: customer research, co-founder dating, and picking the right ballpark
• Why our brains can only hold about 150 relationships
• Why emails and DMs are getting triaged by AI agents, and how to cut through
• Human-led marketing as the moat, and why "your people are your shortcut"
• The liking gap and why the networking drive-by doesn't work
• How Goodword fits into Caroline's Wealth Garden: a wealth of social capital
• "If I could go back to when I started my business, I would tell myself..."

What's your biggest founder confession? Drop it in the comments.

New Founder Confessions episode every week — subscribe for unfiltered startup building lessons.

About the series:

Founder Confessions is a 6-part limited series with candid conversations about responsibility, relationships, and building a company where people still come first.

Hosted by Ashley Grace Jefferson & Sweta Govani.

Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode!

What would make you walk away from a great corporate career?

Sharon Joseph, founder and CEO of CREWASIS.AI, joins Ashley Grace Jefferson for the third of six founder interviews in the Founder Confessions limited series.

After 20 years in marketing and consumer packaged goods, with great salaries and bonuses, she bet on herself. She founded CREWASIS.AI in 2018 and was building in AI before most people called it AI. Today CREWASIS.AI works with brands like Lysol, Enfamil, Centrum and Aquafresh.

Her confession? She thought building the platform would be the hardest part. It turned out to be building the company around it: the team, the right engineers, the right talent at the right time, and the right advisors. It takes a village, and it takes years.

Sharon shares what kept her going when she thought about quitting, why AI hasn’t delivered the instant ROI customers expected, and why her best product ideas come from lunch with customers, not Zoom.

In this episode:

• why building the company is harder than building the product
• how CREWASIS.AI fits into Sharon’s Wealth Garden after 20 years in corporate
• what kept her going: wanting more women and diverse founders in tech
• why AI still takes work, and what that means for enterprise teams
• the AI wrapper problem and the shift from SaaS pricing to credits
• why the best customer insights happen over lunch, not on Zoom
• Sharon shares, "If I could go back to when I started my business, I would tell myself..."

A candid conversation about betting on yourself, building with people you trust, and treating your hardest days as breakthroughs.

About the Founder Confessions limited series

Are you tired of the one-track story to building a scalable business?

Ashley Grace Jefferson & Sweta Govani interview six founders building $2–$4 million+ businesses and ask: “What did you assume about building a business that turned out to be wrong?”

Founders also share how they’re getting closer to their customers, what it’s like building in 2026, and how their business fits into their Wealth Garden.

Seven episodes, released every Thursday starting October 8, 2026. Subscribe to follow the series.

Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode!

What if the biggest thing you give away when you raise isn't money, but control?

Mukund Venkatakrishnan, co-founder of Upfront, joins Sweta Govani for the third of six founder interviews in the Founder Confessions limited series.

His confession? Upfront won the Harvard Business School pitch competition as a crypto company. It isn't one today. And after founding companies before this one, he learned the hard way that founders should fight for every part of the company they can keep.

Upfront builds back office operations and financial services for the real estate industry.

Today it supports more than 80 enterprise accounts, representing 200+ brokerages and 20,000 agents across 38 states and Canada, and processes more than 45,000 transactions a year. The company is a few months away from being cash flow positive, by choice. He shares why he'd rather grow than turn on profit today, why they don't walk in the door as an AI company, and what he'd look for in investors if he could start over.

In this episode:

• how Upfront went from a crypto pitch competition idea to real estate back office and financial services
• why governance and control matter more than your payout at exit
• why the unsexiest businesses are usually the most valuable
• being close to profitable, and choosing growth instead
• building trust in an industry that doesn't want an "AI company"
• what he learns from customers that he could never get from an email or a LinkedIn post
• how Upfront fits into his Wealth Garden, and why he wants to build one for his customers
• Mukund shares, "If I could go back to when I started my business, I would tell myself..."

A candid conversation about ownership, investors, and building the business you actually want to run.

About the Founder Confessions limited series

Are you tired of the one-track story to building a scalable business?

Sweta Govani & Ashley Grace Jefferson interview six founders building 2–4 million+ businesses and ask: “What did you assume about building a business that turned out to be wrong?”

Founders also share how they’re getting closer to their customers, what it’s like building in 2026, and how their business fits into their Wealth Garden.

Seven episodes, released every Thursday starting October 8, 2026.

Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode!

What if the app you’re building is the thing slowing your business down?

MJ Perez, co-founder of Arete Studios, joins Ashley Grace Jefferson for the second of six founder interviews in the Founder Confessions limited series.

Her confession? She thought the app would be the go to market strategy.

They put a lot of money into building a fashion app, and realized they needed to get smarter about where tech fits.

Today, it powers their brand insights and internal processes, as the brand and the tech grow together.

MJ came from machine learning at Uber, and co-founded Arete while still working there. Arete gives shoppers who are tired of mainstream stores a place to find emerging designers from around the world, and gives those designers the infrastructure they need to grow. Arete is now on track for $4.5 million in revenue by the end of 2026. She shares how opening a store in New York changed what they knew about their customers, why she kept her day job until the business could pay her, and why she and co-founder Kotryna Jukneviciute joke it’s IPO or nothing.

In this episode:

• why not every business needs an app
• the moment a tech company realized it needed to be a brand
• why she spends more time on operations than strategy, and how fixing shipping became a new business line
• what a physical store taught them that an app couldn’t
• keeping your 9 to 5 until the business can pay you, and why that can be better for the business
• using AI beyond basic tasks, even if you’re not an engineer
• how Arete fits into MJ’s Wealth Garden and the bar she set before quitting her job
• MJ shares, "If I could go back to when I started my business, I would tell myself..."

A candid conversation about building what your customer wants, not what looks good on a pitch deck.

About the Founder Confessions limited series

Are you tired of the one-track story to building a scalable business?

Sweta Govani & Ashley Grace Jefferson (aka Startup Baddie) interview six founders building $2–$4 million+ businesses and ask: “What did you assume about building a business that turned out to be wrong?” Founders also share how they’re getting closer to their customers, what it’s like building in 2026, and how their business fits into their Wealth Garden.

Seven episodes, released every Thursday starting October 8, 2026. Subscribe to follow the series.

Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode!

What if raising more money for your startup leaves you with fewer options?

⁠Joseph Lee⁠, co-founder and CEO of Supademo, joins ⁠Sweta Govani ⁠for the first of six founder interviews in the Founder Confessions limited series.

His confession? He assumed bigger was always better.

In his first company, he raised too much money before deciding what success meant for him, giving up control and limiting the outcomes he could pursue.

This time, he’s building differently. Joseph shares how he grew Supademo to more than $4 million in annual recurring revenue with $1 million raised, while keeping the business profitable and his options open.

In this episode:

* why raising more venture capital isn’t always better

* how to build a business that gives you options to keep operating, sell or raise more

* why human connection still matters, even in a product-led AI business

* how pricing and the buying experience affect whether customers buy and stay

* staying focused when every new AI launch feels like a threat

* how Supademo fits into Joseph’s Wealth Garden and his evolving definition of success

* Joe shares, " If I could go back to when I started my business, I would tell myself..."

A candid conversation about choosing the business you want to build before committing to someone else’s version of success.

About the Founder Confessions limited series

Are you tired of the one-track story to building a scalable business?

We interview six founders building $2–$4 million+ businesses and ask: “What did you assume about building a business that turned out to be wrong?”

Founders also share how they’re getting closer to their customers, what it’s like building in 2026, and how their business fits into their Wealth Garden.

Seven episodes, released every Thursday starting October 8, 2026. Subscribe to follow the series.

Got something to say to this podcast? Send a voicemail, and you might hear yourself on the next episode!

What we cover:

• introduction & co-hosts own confessions
• takes on business building
• why moving on isn’t always failure
• why surveys don’t mean you know your customer
• what to build when you need money now
• what's to expect from Founder Confessions