When Investors Said No — Twice

The untold stories of two founders who turned “impossible” ideas into market-defining companies.

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This week, we’re spotlighting founders who turned barriers into breakthroughs - from challenging investor bias to surviving a make-or-break pivot and in the process, reshaped entire industries.

Let’s get into it 👇

When Ida Tin set out to build Clue, she wasn’t just creating a company - she was fighting to prove an entire category deserved to exist.

Her vision was bold: a women’s health app that could help people everywhere understand their reproductive health.

But in the early 2010s, “FemTech” wasn’t a recognised industry.

Investors (overwhelmingly male) didn’t see the commercial opportunity.

“I knew we had a good product, people liked it, the team was good, and the numbers were strong.

And still, we would just get no after no. There was some hidden ‘X’ factor.”

That “X” was bias.

Many investors couldn’t connect Ida’s mission to their own lived experience, and she was asking them to back a female founder building in a market they’d never thought about.

How Ida Navigated the Challenge

1. Framing the problem in investor-friendly terms
Instead of pitching Clue as just a “period tracking app,” Ida expanded the narrative.

She positioned it as the first step in a much larger, untapped market: women’s health technology.

  • She highlighted the sheer market size - half the world’s population.

  • She explained the lack of innovation since the contraceptive pill in the 1950s, framing Clue as the long-overdue solution.

  • She used metaphors and analogies to help investors grasp the cultural weight, asking them to imagine the daily impact if every woman could instantly understand her fertility status.

2. Leveraging co-founders to build credibility
Recognising the bias she faced as a female founder, Ida fundraised alongside a male co-founder.

  • This wasn’t about diminishing her role - it was a strategic move to get her foot in the door with investors who were used to backing men.

  • Having male voices in the room helped smooth early investor scepticism and created a bridge of social trust.

3. Creating language for the industry
At TechCrunch Disrupt in 2016, Ida coined the term FemTech.

  • This gave investors a shorthand way to describe and discuss the sector.

  • It helped founders in adjacent areas (from fertility tech to breast pumps) position themselves as part of a recognisable movement.

  • For male investors in particular, it made conversations less awkward: “I’m looking at a FemTech investment” became easier than “I’m looking at a company that helps women with periods.”

4. Sticking to her values
Even under pressure to monetise, Ida refused to compromise on data ethics.

Clue adopted a subscription model rather than selling user data, reinforcing its trustworthiness - a quality investors eventually came to value.

The Results

  • Over 10 million users across 190 countries.

  • First FDA-cleared, 100% data-driven birth control app in 2021.

  • An entirely new sector FemTech - now worth an estimated $60 billion.

Ida’s Reflection

“The biggest hindrance to start is often women themselves. Just start. Then you learn. Don’t wait until you feel ready.”

🎧 Abu Addae (LifeCheq) - The Pivot That Nearly Killed LifeCheq, and Then Made It Unstoppable

For years, Abu and his team at LifeCheq (a financial advisory firm that offers personalized financial advice) poured everything into a consumer-first vision: local offices, a national advisor network, thousands of clients served one-to-one.

Then COVID hit and demand exploded from 400 to 5,000 leads a month.

The problem? They couldn’t scale fast enough.

Worse still, while in the middle of raising a Series A with Naspers Foundry, they realised the only viable path forward was a total pivot to B2B.

“We were mid-raise, with Naspers leading, and had to tell them we wanted to pivot. They said: go figure yourselves out. We nearly died crossing that moat.”

How Abu Survived the Pivot Step by Step

1. Listening to the market, not the plan
LifeCheq’s master plan was clear: build 30 branches, prove the consumer model, then scale with tech.

But when competitors started asking to license their technology, Abu resisted: “We told them to go away. We thought they were the enemy.”

Six months later, he realised the unsolicited demand was the answer they couldn’t ignore.

2. Facing the funding fallout
The timing couldn’t have been worse. Naspers walked away mid-due diligence.

With payroll looming, Abu turned back to existing investors, who agreed to bridge the company on the condition that he retrench staff and focus.

“You can’t do both. You can’t pursue one vision while trying to build another. At Series A stage, you don’t have those resources.”

3. Reframing the team as a new asset
Letting people go was brutal. But Abu saw hidden strength: the very advisors they’d hired could now train thousands more via the platform. What looked like a painful reset became the seed of a scalable supply side.

4. Leading founder-first sales
Pivoting meant entering an entirely new business model - B2B enterprise sales.

Abu leaned on his Old Mutual reputation and personal network, stepping back into the arena himself. 

“At that point, it had to be founder-led sales. These were people I’d worked with for years. They needed to see me at the table.”

The Outcome

  • LifeCheq survived the Series A fallout, won back Naspers as a lead investor at a higher valuation, and closed the round in 2022.

  • It became South Africa’s largest advice platform, used by thousands of financial advisors.

  • The company reached cashflow profitability and is now expanding into emerging markets.

Abu’s Advice for Founders

  • Trust the signals: “Don’t die standing still. If the market is beating you over the head with an answer, listen.”

  • Be capital efficient: “Only spend when you see the metrics move. You can do a lot without spending.”

  • Respect regulation: “In this industry, break one thing and you could go to jail.”

  • Protect your health: “Money comes and goes. Your health doesn’t.”

📚 Interesting Reads & Resources

  1. Barclay Eagle Labs x Ford Family Foundation: opportunity for social entrepreneurs from UK universities to win funding

  2. Amazon Web Services Impact Bootcamps powered by Techstars

  3. Hacker Room Cohort 2: 4-month residency for technical & ambitious work

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