Founder F**K ups

She was the expert in the room. Then the experts nearly sank her company.

So-Young Kang has a Harvard MBA, spent years at McKinsey, and was named a World Economic Forum Young Global Leader. She built Awaken Group, then left the CEO seat to go all in on Gnowbe, a SaaS platform co-founded in San Francisco and Singapore at the same time.

As a first-time tech Founder, she did what smart leaders are supposed to do. She built an advisory council of investors and experts on both sides of the Pacific. Silicon Valley told her to grow at all costs. Singapore asked when she'd be profitable. She was pulled between two cultures, and every strategy she believed in got questioned until she stopped believing in it.

So she took half steps. Half steps gave half results. Half results meant more advice. Seven years in, in 2023, Gnowbe was nearly bankrupt.

She lined up three acquisition offers in two weeks. A week before signing, one of her employees told her, in tears, not to sell. So she didn't. She disbanded the council, cut the company by more than half, and got it cash-flow positive in under a year. Then she rebuilt the whole platform around agentic AI.

This one gets into:

• Why she built an advisory council in the first place, and what it got right
• Silicon Valley's "grow, grow, grow" vs Singapore's "when are you profitable?"
• Growing up never being told you're wrong, then moving to a culture that questions everything
• The spiral of doom: half commitment, bad results, more advice
• Three offers, a three-day prayer fast, and the employee who said "don't sell"
• How to tell your advisors it's over without burning the relationship
• Cutting 50%+, protecting cash, and doubling down on existing customers
• Her three filters for deciding whose advice to take
• Why your identity can't be your startup

A Founder who spent her career advising others, and learned the hard way how to take advice.

If you've got five advisors telling you five different things and your gut is saying something else, watch this one.

CHAPTERS 00:00 Harvard, McKinsey, and nearly bankrupt 01:09 Building Gnowbe in San Francisco and Singapore at once 02:23 Why she built an advisory council 03:52 Silicon Valley vs Singapore: growth or profit? 07:41 "My whole life, I was never told I was wrong" 09:15 Why Founders in Asia hide their mistakes 10:42 Half steps: how the doubt crept in 12:50 2023: nearly bankrupt, three offers in two weeks 13:46 A week before signing: "Don't sell the company" 15:45 Two miracles 17:44 The spiral of doom 19:05 Disbanding the advisory council 20:48 How to tell your advisors it's over 24:11 Cut 50%, protect cash, double down on existing customers 25:20 Rebuilding Gnowbe as an agentic AI platform 27:11 The first sign it was working 30:27 Three filters for whose advice to take 33:18 The B2B vs B2C trap 35:44 Your identity is not your startup

GUEST So-Young Kang, Founder & CEO, Gnowbe | Founder, Awaken Group LinkedIn: https://www.linkedin.com/in/soykang/ Website: https://www.gnowbe.com

FOUNDER F**K UPS The podcast where Founders talk about the thing that actually went wrong. Website: https://www.founderfuckups.co YouTube: https://www.youtube.com/@founderfuckups

#founders #startups #founderstories #advisoryboard #startupfailure #saas #singaporestartups #southeastasia #gnowbe #entrepreneurship

Pav Gill blew the whistle on Wirecard. Singapore VCs still treated him like he was too local.

As General Counsel for Wirecard’s Asia-Pacific region, Pav found what he wasn’t supposed to find. He spoke up, lost his job, and watched one of Europe’s biggest corporate frauds collapse. Then he built Confide, an all-in-one agentic governance, risk and compliance platform designed to replace the patchwork of legacy tools most companies rely on.

When Confide launched, the Financial Times, Wired, Dow Jones and Business Insider covered it. VCs from London, Europe and the US came calling. In Singapore, his home market, there was nothing.

Pav calls it the Charles & Keith effect. In Singapore, a local product starts at a quiet discount to a Western one. Local Founders are told to drop the “Singapore company” positioning, go abroad, prove themselves, and only then come home to get backed. He ended up raising around $3M in pre-seed from GRC leaders, lawyers and compliance chiefs around the world. Now that it’s time for his seed round, the question is whether he raises it here at all.

This one gets into:
→ Why local VCs go looking for reasons not to invest within five minutes
→ The Asian uncle who isn’t impressed by your Olympic gold
→ Pre-seed conversations that turn into ARR conversations
→ Grants that make you spend $50K before you get $50K back
→ Why backing your own Founders only after they’ve succeeded is “taking the icing on the cake”
→ What happens to the Founder who doesn’t have a Wirecard story to open doors

A lawyer turned whistleblower turned Founder who wants Singapore to back its own from day one.

If you’re building in Singapore or Malaysia and wondering whether you have to leave to get taken seriously, watch this before your next pitch.

CHAPTERS
00:00 Who is Pav Gill?
00:54 Global press, zero local interest
02:56 The UK’s EIS vs Singapore’s grant maze
05:31 The Charles & Keith effect
08:24 “Why should I not invest in you?”
09:25 The Asian uncle problem
10:06 Pre-seed, but show me your ARR
13:01 Why prove-it-abroad-first is backwards
13:44 Raising $3M from GRC leaders
15:45 What if you don’t have a Wirecard story?
18:28 Grants that need you to have the money first
21:30 The Hague said yes, Singapore said two years of audited accounts
24:22 Who should move first?
25:22 Scouting Founders like football talent
30:00 Stay or go? Pav’s advice to local Founders

GUEST
Pav Gill, Founder & CEO, Confide
LinkedIn: https://www.linkedin.com/in/pavgill/

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 #Singapore #VentureCapital #Founders #Fundraising #Wirecard #StartupEcosystem #SoutheastAsia #GRC

He spent thousands of ringgit on Meta ads. The leads came in, then went quiet.

Maurizio Rosini spent 17 years in fashion with Prada and Gucci, rode the highs of money and fame, and came back from addiction. He now runs My Masterman, the men's circles that a thousand men have been through in four years across Kuala Lumpur, Penang and abroad.

But when he took it to paid ads, he hit a wall. Men messaged, he replied, and then nothing. He was asking cold strangers to sign up for a room they couldn't picture, and assuming 10 out of 10 should say yes because he was convinced.

The fix wasn't more leads. It was one open question, a landing page, and putting 20% of the ad budget into education that isn't meant to convert.

This one gets into:

• Why a lead that messages you isn't a conversation yet
• Boosted reels, a PDF people thought was a scam, and DMs that don't scale past 100 leads
• "Is this a gay thing?" and why social proof answers it better than you can
• The open question he now sends every new lead
• Spending 20% of your budget on awareness, and why nurtured leads end up costing nothing

An ex-luxury exec turned men's coach who still says "fuck" when it matters.

If you're paying for leads that never turn into conversations, start at 13:44.

CHAPTERS
00:00 Maurizio's story in 60 seconds
00:59 Why admitting a fuck up is harder for men
03:14 From Prada and Gucci to addiction, and the pattern he saw in men
06:15 Why a circle: shoulder to shoulder, you can't hide
07:38 How do you get men to drop the armour?
11:42 From experiment to My Masterman
13:44 The mistake: thousands on ads, no way to convert
15:05 Reels, PDFs, "is this a scam?": everything he tried
16:32 "Is this a gay thing?" and why social proof matters
17:00 The one question that starts the conversation
17:54 B2C or B2B, outreach is about starting a conversation
19:28 Did he ever think he was building the wrong thing?
24:39 Educate first, ask second: 20% of budget on awareness
29:04 Does nurture bring acquisition cost down?
31:37 One piece of advice before you run ads
32:24 Where to find Maurizio

GUEST
Maurizio Rosini, Founder, My Masterman (men's circles, retreats, coaching)
LinkedIn: https://www.linkedin.com/in/mauriziorosini/
Instagram: @mymasterman.coach

FOUNDER F**K UPS
The podcast where Founders talk about the thing that actually went wrong.
https://www.founderfuckups.co
https://youtube.com/@founderfuckups

#founders #startups #leadgeneration #metaads #salesfunnel #menscircle #founderfuckups

He spent 20 years assessing risk for Malaysia's banks. Then he hired his friends.

Firdaus Mohamed built a career on one skill: knowing what could go wrong. Corporate strategy at Bank Islam, Zurich, Etiqa and AmBank. Credit committees. Zakat committees. Then he left to build GoBarakah, a fintech that turns donations into trackable, traceable e-vouchers, and his team went on to launch Impakrintas, Malaysia's first Social Exchange.

But when it came to his own team, the risk expert skipped the due diligence. A conversation over Hari Raya dinner became a job offer. An old uni friend with C-suite banking experience came in as his number two. Within a month the red flags were obvious. She wouldn't talk to the CTO. She turned 30-second decisions into 30-minute phone calls. She showed up two hours late to a government meeting he'd sent her to in his place.

Then he did it again. A friend who needed a break came in as an intern, and after she left, the business found out she'd been messaging clients behind their backs to undermine the founders. It ended with a letter under threat of legal action. And the friend was his wife's. His wife is also his CTO.

This one gets into:

• Why the people you trust most can be your worst hires
• The red flags that show up in month one, and why Founders ignore them
• What protecting a friend tells the rest of your team
• Managing someone you'll see at the next family dinner
• The hiring process he runs now: hire slow, fire fast
• Why big-company experience doesn't transfer to a startup

A banker who learned the hard way that a great CV and a great friendship don't add up to a great hire.

If you're about to bring your best mate into the business, watch this first.

CHAPTERS
00:00 Intro
00:54 Why a risk expert didn't apply it to hiring
01:47 From Hari Raya dinner to job offer
02:59 The ex-bank C-suite friend
04:34 Red flags in month one
06:16 How long it took to act
07:26 The 30-minute phone calls
08:37 Two hours late for a government meeting
10:33 Why he kept giving chances
11:52 What the team saw
13:07 Hire number two: the intern
15:42 The letter under threat of legal action
18:12 When the friend is your wife's
19:11 What happened to the friendships
23:55 How he hires now
26:21 Tying pay rises to probation
26:39 His advice: don't hire your best mate
29:08 Why bank experience doesn't transfer
30:31 Every salary transfer hurts

GUEST
Firdaus Mohamed, CEO & Co-founder, GoBarakah and Impakrintas
LinkedIn: https://www.linkedin.com/in/firdaus-mohamed-289b576/
Website: https://impakrintas.com

FOUNDER F**K UPS
The podcast where Founders talk about the thing that actually went wrong.
Website: https://www.founderfuckups.co
YouTube: https://www.youtube.com/@founderfuckups

#FounderFuckUps #Founders #Hiring #StartupMistakes #HireSlowFireFast #Malaysia #Fintech #Leadership #StartupCulture

She hired hundreds of people. Most of them gave her one good year.

Kim Lim co-founded PichaEats in 2016 with two fellow volunteer teachers, to keep refugee kids in school. Refugees can't legally work in Malaysia, so PichaEats lets refugee chefs cook from home and get paid properly for it. Ten years on, they've partnered with 45 chefs from 7 countries and fed clients like Google, AMEX and Bank Negara.

But a company built on heart got hired on heart too. Early hires were friends of friends, or people the team could vibe with. Mission-driven people joined, then found out it was a food business with targets, not mission work.

The real wake-up call was the maths. People stayed about two years. Training took the first 3 to 4 months, and the last 6 months they'd already checked out. So PichaEats got about one year of full performance from each hire, then started again.

What fixed it was a coach, a rebuilt set of values, an employee handbook the old team hated, and an HR hire before anything else when it was time to scale. Average tenure is now 3 to 4 years.

This one gets into:
→ Why "we can vibe with them" is not a hiring criteria
→ The trap of hiring people who love the mission but can't do the job
→ How to let go of someone who genuinely cares
→ The one-good-year maths most Founders never run on their own team
→ Why her first hire for scaling was HR
→ The four values every PichaEats hire now has to hit, and why they always check references

Kim is one of the most honest Founders I've had on about the cost of leading with your heart.

If your best people keep leaving at the two-year mark, watch this before your next hire.

CHAPTERS
00:00 Kim's story
01:11 Why a food business?
03:42 The mistake: hiring on feeling
06:10 When the mission makes you a worse judge of talent
07:57 Letting go of people who care
10:30 The two-year problem: one good year per hire
12:10 Bringing in a coach and rebuilding the values
13:12 Why the first scaling hire was HR
14:49 Tenure now: 3 to 4 years
16:17 The uncomfortable part: professionalism and the employee handbook
17:56 How PichaEats hires now
19:11 The culture-fit checklist

GUEST
Yuet Kim Lim, Co-Founder & CEO, PichaEats
LinkedIn: https://www.linkedin.com/in/picha-kimlim/
Website: https://www.pichaeats.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 #Founders #Hiring #CompanyCulture #SocialEnterprise #StartupMalaysia #PichaEats #Leadership

One in five startups dies of co-founder fallout. Most co-founders at least go home to different houses.

Lyv and Paul go home to the same house, and the same dog.

They met through a work enquiry that produced no business whatsoever. Seven years later they were married, and three months ago they opened The Contrast Club, an ice bath and sauna studio in Kuala Lumpur. So for this episode we did the whole thing inside their own protocol. Coffee at the bar, questions in the sauna, rapid fire in the plunge, and the honest stuff in the magnesium bath.

Ten weeks after opening they had to shut the doors for four days and strip out work they'd already paid for. The part Paul admits in the ice bath is the part that makes it a Founder F**k ups episode: they could see it coming and kept going anyway.

This one gets into:

• Why a second yes matters more than the first one, and how Lyv knew Paul was finally in
• What actually happens when two people who work at different speeds run one business
• Selling a habit instead of a treat, and why that's a business model problem rather than a marketing one
• The packages that didn't sell, and what they changed
• Why people who come with a friend buy again more often
• Closing a three-month-old business for four days on purpose
• Whether a couple's session ever stays a couple's session

Lyv and Paul are the rare pair who answer the co-founder question honestly rather than sweetly.

If you're thinking about starting something with your partner, watch the last five minutes before you do.

CHAPTERS

00:00 A work enquiry that led to no business

01:00 The dinner table, and Paul's hesitation

02:10 The second yes, and how Lyv knew

03:45 The walkthrough: what they took from onsens, bathhouses and New York

05:30 What contrast therapy actually does

07:00 Why founders in particular need somewhere to put it

08:20 The paint job, and closing four days in month three

10:10 Habit, not treat: the retention problem

13:00 What didn't sell, and the fix

14:20 Two speeds: the event that went sideways

15:30 Does it stay out of the house?

17:00 Rapid fire, three degrees

19:25 The magnesium bath: it always turns into a meeting

21:30 Advice to a couple thinking about it

GUEST

Lyv & Paul, co-founders, The Contrast Club, Kuala Lumpur

FOUNDER F**K UPS

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

www.founderfuckups.co

youtube.com/@founderfuckups

#founderfuckups #startups #cofounders #kualalumpur #contrasttherapy #icebath #smallbusiness #foundersjourney #malaysia #entrepreneurship

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