In 2022, Wes Barnes had everything a Founder is supposed to need. He just had no way to build it.

Wes spent 15 years in private equity. He built and sold a fund platform he had been quietly trying to make smarter with AI back in 2018, years before anyone was calling that a category. When he started again he knew the customer, because he had been the customer. He had a network that opened doors to VCs and buyers. And the smartest people around him agreed the idea was good.

He is not technical. People told him to go and find a technical co-founder. He heard them and decided it could wait, because he had managed dev teams before and figured he could manage some more. So he went to dev houses instead.

A dev house delivers the scope and nothing else. Every change is an expansion and another quotation. And 2022 was the year the whole industry moved from machine learning to generative AI, so the product kept changing underneath him while he was paying by the scope. He ended up faking demos in CustomGPT just to have something on a screen. In every meeting, once everyone had agreed the opportunity was real, came the same line: okay, but can you show me the product?

That cost him the best part of a year.

This one gets into what that year actually bought him. Why the dev shop model is built for companies that already have technical people to manage it, and breaks at startup speed. The pivots he paid for twice. The long dating period with the co-founder who eventually reached out to him, and the values conversation that convinced them both. What happened in the first ninety days: a team he could never have recruited on his own, an MVP in six months, a commercial product six months after that. How they split equity when one of them had already spent the money, and why "until you have something, you have nothing" was the only way he could look at it. And the poker question he now asks before he spends a single cent.

Wes is a Founder who did everything right except the one thing everyone told him to do.

If you are about to sign with a dev house, or you have convinced yourself that Cursor and Lovable mean you can skip the technical co-founder, watch the last ten minutes twice.

CHAPTERS
00:00 "Can you show me the product?"
00:15 Selling venture one and starting again
04:21 The advice he heard and parked for later
06:33 Why a dev house instead of a co-founder
09:50 "That model is not designed for startups"
11:03 Faking demos with CustomGPT
13:47 The meetings where the idea was never the problem
17:39 The long dating period with Vishal
21:29 What changed in the first ninety days
23:36 "Until you have something, you have nothing"
26:51 Could Replit and Lovable have saved him?
30:05 The poker question before you spend a cent

GUEST

Wes Barnes, Founder, Associum
LinkedIn: /in/wesleybarnes2

FOUNDER F**K UPS

The podcast where Founders talk about the thing that actually went wrong.

Website: https://www.founderfuckups.co
YouTube: /@founderfuckups

#FounderFuckUps #Startups #Founders #CoFounder #PrivateEquity #AI #DevShop

In 2016, Chris J Reed was worth 67 million euros.

He couldn't touch a single one of them.

Chris had built Black Marketing from nothing in Singapore. Three profitable years in, one of the founders of a roll-up called The Marketing Group approached him with a plan: buy four agencies, list on the Nasdaq in Sweden, scale everybody. Chris said yes. He owned 25% of a company that hit a quarter of a billion euros in market cap inside two months.

Then he tried to borrow against it. Ten banks said no. Not one of them thought it was a substantial company.

While the share price was climbing, the actual business wasn't. The promised synergies didn't exist, because the other agencies were B2C and he was B2B. He was flying to Sweden, drinking champagne and ringing the bell, and firing his own staff in a Singapore co-working space at the same time. His team thought he was a millionaire and had stopped trying.

Then his divorce lawyers found the Nasdaq listing. The first draft of the settlement had him paying his ex-wife ten million dollars against money that did not exist. He renegotiated when the share price collapsed, but it started from an artificial number, and he is still paying against it ten years later.

This one goes deep on what a roll-up actually costs a Founder. The deals announced on the Nasdaq before they were signed. The Sydney hotel meeting where Chris congratulated two agency founders on joining the group and they had no idea what he was talking about. The 19 missed calls and the threat to report him to the police. Three CFOs in a single year. And how he got out: closing the Singapore entity they had bought, moving every client into the Hong Kong entity they hadn't, and rebuilding leaner with teams in the Philippines and South Africa.

Chris is a Founder who ended up worth less than he sold for, spent what was left on lawyers, and had to explain to every new prospect why his company still existed. He built the brand back anyway.

If you have a term sheet, an earn out or a lovely paper valuation sat in your inbox right now, watch the last ten minutes twice.

CHAPTERS

00:00 67 million euros he could never touch 01:35 "There's a Nasdaq in Sweden?" 06:47 25% of a quarter of a billion 08:01 Ten banks said no, and he ignored it 10:21 Ringing the bell while firing staff 11:52 The synergies that never existed 12:41 When your divorce lawyer finds the share price 14:56 Sydney: the deals that hadn't actually happened 17:33 19 missed calls and a threat to call the police 20:11 Founders out, bean counters in, shares under one euro 22:18 They bought Singapore. They didn't buy Hong Kong. 24:19 "You're fired, you're fired, you're fired" 26:10 When Google becomes your biggest objection 27:48 The question to ask before you sign anything 32:15 What he'd do differently

GUEST

Chris J Reed, Founder & Global CEO, Black Marketing LinkedIn: https://www.linkedin.com/in/theonlyceowithamohawk/ Black Marketing: https://blackmarketing.com

FOUNDER F**K UPS

The podcast where Founders talk about the thing that actually went wrong.

Website: https://www.founderfuckups.co YouTube: https://youtube.com/@founderfuckups

#FounderFuckUps #Startups #Founders #Singapore #Nasdaq #Acquisition #LinkedIn

Glenn Tan is co-founder and CEO of Zavior, the Singapore RegTech using AI to get teams compliance-ready on PDPA, ISO and everything buyers ask for.

He is a sales and partnerships founder. So he did what almost every non-technical founder does: he left the building to the person who builds. Then the product ran badly behind, the money ran out, and his technical co-founder left.

Two options. Ship fast or shut it down. Glenn took over the tech himself while still running sales, delivery and partnerships, and inside a year they built every feature they had wanted since day one.

This one is about what it costs to outsource the thing your company is made of, and what you find out about yourself when the floor goes.

Takeaways

• "Almost there" is the warning sign. Every almost there hid two more things to do, and they piled up while he kept selling what was still in progress.
• His co-founder leaving was not dramatic and not personal. It was money plus a gap too expensive to close.
• Talking to more people can be a way of delaying the call. At some point it is your decision and nobody else's.
• The blocker was never the tech. It was fear of starting things that used to take too long.
• Domain expertise is the new advantage in building. If you know what the client wants, you can now build it yourself.
• Build the functionality of the city first, then the piping.

Chapters

• 00:00 Losing a CTO with no runway left
• 01:12 Clients on the books, product way behind
• 03:43 What the delay did to the money
• 04:33 Climb Everest, or take the helicopter
• 05:40 He builds, I sell, and the first cracks
• 06:33 The "almost there" trap
• 07:49 Did you see the quit coming?
• 08:58 Money or product: the real breaking point
• 09:35 The first ten seconds after "I'm out"
• 10:43 Ship fast or shut it down
• 12:49 The conversation with his wife
• 15:13 Why he picked up the tech himself
• 17:05 Cursor, and fear as the actual blocker
• 18:10 Three to six months of hammering
• 20:47 "I lost a limb, but I'm on a rocket ship"
• 21:08 Why domain experts are the best builders now
• 25:57 For the founder one resignation away

Dan Gericke, co-founder of Shift Control and former CTO at Express VPN, shares his experience with AWS partnership, compliance challenges, and the impact on sales. The conversation explores the partnership mirage, compliance issues, and the importance of early sales cycles. The conversation delves into the challenges and insights of partnering with AWS and the impact on a startup's growth. It explores the ROI, time investment, and considerations for founders when entering a partnership program.

Takeaways

• Partnership Mirage
• Compliance Challenges Partnership programs like AWS require significant time investment and may not yield immediate ROI.
• Founders should focus on direct sales and partnerships, avoiding distractions from ecosystem partnerships.

Chapters

• 00:00 The AWS Partnership Mirage
• 03:03 The Compliance Challenge
• 12:50 Navigating the Sales Cycle
• 17:52 The ROI of Partnership
• 18:21 Navigating the AWS Ecosystem
• 19:06 Challenges of Startup Partnerships
• 26:01 The Impact on Product Development
• 30:32 Considerations for Founders

The conversation delves into the challenges of bad hiring choices, the impact of bad hires on business growth, the consequences of lowering the hiring bar, the cost of bad hires and self-doubt, overcoming hiring mistakes, rebuilding the recruitment process, assessing critical thinking and problem-solving, the importance of methodical hiring, and lessons learned for moving forward.

Takeaways

• The importance of owning the recruitment process as a founder of a small team
• The need for methodical hiring and assessment of critical thinking and problem-solving skills

Chapters

• 00:00 The Pitfalls of Bad Hiring Choices
• 03:01 The Impact of Bad Hires on Business Growth
• 05:58 Lowering the Bar and Its Consequences
• 09:02 The Cost of Bad Hires and Self-Doubt
• 12:01 Overcoming Hiring Mistakes and Building Confidence
• 15:04 Rebuilding the Recruitment Process
• 18:05 Assessing Critical Thinking and Problem Solving
• 20:53 The Importance of Methodical Hiring
• 24:02 Lessons Learned and Moving Forward

Lizzy Tan, co-founder of Cleve AI, shares her experience with the co-founder commitment gap and the challenges of early stage recruiting. She discusses the impact of juggling multiple responsibilities and the importance of effective communication in building successful business relationships.

Takeaways

• Co-founder commitment gap
• Effective communication is key

Chapters

• 00:00 Introduction and Co-founder Commitment Gap
• 06:06 Recruiting a Technical Co-founder
• 12:00 Challenges of Juggling Responsibilities and Communication

Are you a founder constantly looking for the "next big thing"? You might be suffering from Shiny Object Syndrome. In this episode of Founder F**k Ups, Ben Bagg sits down with Adam Chambers, serial entrepreneur and founder of Nurse Recruitment Experts, to discuss the dangerous trap of chasing new ideas instead of focusing on what actually works.

Adam shares his costly $7,500 mistake of investing in a new job board that yielded zero results, and how it distracted him from his core business engine. We dive deep into the opportunity cost of lost focus, the importance of doubling down on proven strategies, and why the most boring advice in business is often the most profitable.

If you're a founder struggling with focus, hiring mistakes, or knowing when to kill a failing experiment, this episode is packed with actionable insights to help you stay on track.

Key Takeaways:
•Why doubling down on your core engine beats chasing new channels.
•The real cost of Shiny Object Syndrome isn't just money—it's lost time and focus.
•How to know when to pull the plug on a failing experiment or bad hire.
•The importance of matching your offer to market demand (and the Mexican Fish & Chips analogy!).
•A practical framework for calculating ROI and the cost of inaction before starting new projects.

Chapters
0:00 - Introduction: The Trap of Shiny Object Syndrome
0:37 - Adam's $7,500 Mistake: Investing in the Wrong Job Board
2:29 - Why Doubling Down Beats Chasing New Platforms
4:13 - The Role of Emotion vs. Logic in Sales and Investments
5:21 - Recognizing Vanity Metrics and Failing Experiments
7:11 - Hiring Mistakes: The Cost of Distracting Your Team
9:06 - The Real Tragedy: Lost Time and Compound Effects
11:25 - The $5 vs. $500 Task Framework for Founders
12:23 - How to Know When to Pull the Plug on a Bad Hire
15:16 - Interviewing for Culture and Behaviors
17:48 - The Most Important Thing: Supply, Demand, and Your Offer
19:50 - The Mexican Fish & Chips Analogy: Market Misalignment
21:44 - Why Founders Avoid Speaking to Customers
23:49 - A Framework for Calculating ROI on New Initiatives
26:34 - Valuing Your Time and the Cost of Inaction
30:14 - Final Advice for Founders: Protect Your Profits and Do the Math

#ShinyObjectSyndrome #FounderMistakes #BusinessGrowth #Entrepreneurship #StartupAdvice #Focus #ROI #HiringMistakes #FounderFuckups #BusinessStrategy #AdamChambers #BenBagg

The conversation delves into the proven hypothesis trap, the challenges of solving the scheduling problem, the pivotal moment of pivoting the business, and the strategy of building in public. Jing Jing shares insights on the pitfalls of assuming a proven hypothesis, the complexities of scheduling solutions, the need for pivoting to address customer needs, and the benefits of building a business in public.

Takeaways

• Proven hypothesis trap
• Solving the scheduling problem
• Pivoting the business
• Building in public

Chapters

• 00:00 The Proven Hypothesis Trap
• 11:07 Pivoting the Business
• 20:06 Building in Public

Admond Lee, founder of The Runway Ventures, shares insights on the five most common red flags that signal a startup's path to failure. These red flags include growing too fast, spending too much, pivoting too slow, an unsustainable business model, and lack of governance. Admond provides examples and practical advice for founders to avoid these pitfalls.

Takeaways

• Pattern recognition is crucial for identifying red flags in startup failure.
• The impact of lack of governance can be significant, especially when dealing with multiple stakeholders.

Chapters

• 00:00 Identifying Red Flags
• 07:08 Spending Too Much
• 15:04 Pivoting Too Slow
• 23:05 Unsustainable Business Model
• 30:25 Lack of Governance

Tiffany, the founder of WeAssist, shares her experience with the Founder's Fix-It Trap, the process of restructuring her company, and the shift in leadership and empowerment. The conversation delves into the challenges faced by early-stage founders and the transformation of leadership style to build a successful team.

Takeaways

• Founder's Fix-It Trap
• Building a Team
• Leadership and Empowerment

Chapters

• 00:00 Introduction to WeAssist
• 11:11 Restructuring the Company
• 19:56 Skill Gap Analysis and Restructuring
• 28:02 Leadership and Empowerment