Discover/Riding Unicorns

Markeplaces, hard truths and angel investing with Mandeep Singh, ex-Founder @ Trouva (acq by Made.com).

Riding UnicornsMandeep Singh — an angel investor and co-founder and former CEOFeb 12, 202546 min

Mandeep Singh pulls no punches about the brutal realities of marketplace building, from discovering that most boutique owners couldn't even generate basic website traffic to the dangerous founder tendency to ignore customer feedback like they ignore investor rejection. His contrarian take on angel investing—that founders from only successful backgrounds lack the grit needed for real challenges—offers a refreshing perspective from someone who's lived through both the highs of acquisition and the lows of near-failure.

Key takeaways

  • •Most early-stage founders are solving fake problems—if customers are only getting five sales on their existing website, building them a marketplace won't magically create demand.
  • •Founders develop dangerous immunity to rejection from investors that can spill over into ignoring critical customer feedback.
  • •Don't overthink angel investment valuations—you'd happily pay 100% more for your eventual winners, so focus on backing the right founders instead.
  • •Be wary of founders who've only experienced success at unicorns—the grit required for early-stage challenges comes from experiencing real failure and setbacks.

Listen to full episode

0:00
marketplacesangel-investingfounder-journeypivotingb2b-saas

Best moment

3:35· 18sfounder story

Five sales ever: The brutal reality most founders won't admit

3:35 / 3:53

They were like, what the are you talking about? Alright. What are you talking about? I've got some website, you know, I've got Magento or Shopify website, and I'm getting, like, five sales. Okay. Five sales a day, five sales a week? Alright. No. Five sales ever. And then I said, well, what are you doing to promote it?

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“And then believe when everyone tells you that it's a silly idea.”

at 7:12

5 clips

Ordered by timestamp. Jump to the moment you care about.

Riding Unicorns · Mandeep Singh

founder story

Five sales ever: The brutal reality most founders won't admit

Mandeep Singh reveals a harsh conversation with struggling e-commerce founders who had unrealistic expectations about their online stores. He exposes the gap between what founders think they're achieving versus the brutal reality of their actual performance, highlighting the common mistake of building without promoting.

3:35 - 3:5318s
ecommerce-realityfounder-delusionmarketing-basics

Riding Unicorns · Mandeep Singh

founder story

Why building a marketplace website isn't solving the real problem

Mandeep Singh explains how Trouva initially misunderstood their customers' needs by building a website solution when the real problem independent retailers faced was lack of scale, not lack of digital presence. He uses the 'Field of Dreams' analogy to describe the common startup mistake of building something without validating the actual problem.

3:54 - 4:0916s
problem-validationmarketplace-dynamicsstartup-mistakes

Riding Unicorns · Mandeep Singh

personal lesson

The dangerous moment when founders start ignoring customers like they ignore investors

Mandeep Singh reveals a critical founder mistake: applying the same "ignore the doubters" mindset used with rejecting investors to actual customer feedback. He explains how this led his team to dismiss legitimate customer requests for delivery and expansion, confusing necessary founder resilience with harmful customer blindness.

7:12 - 7:5038s
customer-feedbackfounder-mindsetproduct-decisions

Riding Unicorns · Mandeep Singh

Bold/Contrarian

I have a negative reaction to founders who have only ever seen, like, success or positivity... you are seeing founders coming from very successful unicorns or decacorns

This is a provocative take on founder backgrounds that challenges the current trend of hiring from successful companies. The contrarian framing ('negative reaction') makes it highly quotable and debate-worthy.

34:14 - 34:4228s

Riding Unicorns · Mandeep Singh

tactical advice

Don't overthink angel deals - you'd happily overpay 100% on your winners

Mandeep Singh shares a crucial lesson for angel investors about not talking themselves out of great deals. He argues that for true winners, the returns are so massive that overpaying by 100% wouldn't matter - whether you got in at $5M or $20M valuation becomes irrelevant when the company becomes a unicorn.

39:16 - 39:5640s
angel-investingvaluationinvestment-psychology

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