How to Lose Sales and Alienate People: The Worst (and Best) Business Pitches



Writer Alyssa Jaffer rounds up the best – and worst – brand business pitches, plus reveals what makes a winning business pitch from founder Victor Riparbelli, CEO of Synthesia, and VC investment manager Hannah Tapsell Chapman.
Ask any Dragon’s Den fan for the worst business pitch of all time and many will say it’s Flow Signals – crowned on TV as the “worst invention ever.”
Pitching his invention of LED lights on traffic signs, founder Derek Cozens had the dragons bewildered. He failed to demonstrate any market demand for his invention, he did not have a viable business model and he admitted he was refused the regulatory approval he would need.
By the end of the Q&A, the dragons were begging him not to invest more of his own money into the business.
Don’t be like Derek.


In a marketplace where 90% of startups fail➚, most entrepreneurs don’t get their idea off the ground because their value proposition is presented poorly. But there’s a tool that can make or break your business in the early days, and it doesn’t cost a thing.
It’s your business pitch.
From Dragon’s Den to Series D, we’re diving into the worst and best business pitches. Plus, we’re spilling the secrets on what it really takes to pitch your business successfully.
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Learn from failure – even when it’s not your own
So Flow Signals wasn’t the best idea – but it’s not the only business to get it wrong at the pitch presentation. Another contender for the worst business pitch is Amber, a phone-charging dock with fingerprint scanning technology for the “reasonable” cost of $1,000.
During a particularly painful grilling➚➚ on Shark Tank, the US equivalent of Dragon’s Den, investor Kevin O’Leary said to Amber’s founders: “I have to hire you both so I can fire you. This is so horrible… I hate this so much it’s incredible. It’s one of the worst ideas I’ve ever seen. I’m out.” The extremely high price point, fallible tech and failure to show why anyone would need the product ultimately doomed Amber’s pitch.
And you might remember blood-testing company Theranos, founded by Elizabeth Holmes. Despite successfully raising $1.4 billion, the pitch deck had a critical flaw – it over inflated the projected value of the business. Holmes’ claim when fundraising that her technology could diagnose disease with just a few drops of blood was revealed to be untrue, and she was sentenced to prison for defrauding investors.
From pitch to rich: How to skyrocket success
According to 2024 data from DocSend, investors spend an average of just 2 minutes and 18 seconds reviewing a pitch deck. That means you have a small window to make a big impression.
“If due diligence is the interview process, then the pitch deck is the CV,” said Hannah Tapsell Chapman, an investment manager at Mercia Ventures, one of the UK’s most active venture capital firms. “While there is a lot that goes into the overall assessment of whether to invest, the pitch deck is what gets you through the door in the first place.”
Your pitch deck is an opportunity for you to tell a rich story about you and your business – who you are, what problem you’re solving and why.
Case in point, before Airbnb was a household brand, in 2008 the business had a simple 10 slide deck which helped founders Brian Chesky, Joe Gebbia and Nathan Blecharczyk unlock $600,000 in funding – and eventually become a billion dollar business.
And it’s easy to see why. The original AirBed&Breakfast deck is simple and not crowded and it takes investors on a journey through the problem, solution, market landscape, business model and competitive advantages.
LinkedIn co-founder Reid Hoffman lifted the veil on his 2004 pitch deck, explaining how it helped his team raise $10 million in Series B funding. He even acknowledges the “mistake slide” which didn’t belong in an investor pitch.
Another example of a winning pitch deck is Tinder, then known as Matchbox. The pitch deck was a breath of fresh air, a departure from the usual using humour, imagery and a compelling story to sell the company’s vision. And it worked. Tinder raised more than $50 million in three rounds of funding.
What not to do when pitching your business
When seeking funding for your venture, it’s important to be intentional and targeted with investors you’re courting.
“One common deal breaker is a fundamental mismatch between the business and the fund’s mandate,” said Chapman. “If you’re seeking £30 million, don’t approach a fund that only writes £500k cheques. And if you’re a B2C business, avoid targeting a deep tech fund.”
And when preparing and presenting your pitch deck, there are lots of ways to get it wrong. Common pitfalls include making it too long and overly complex and failing to explain your go-to-market strategy.
AI video platform Synthesia’s CEO and co-founder Victor Riparbelli said: “Our pitch deck focused on three key themes: What sets Synthesia apart in an increasingly competitive space, the value proposition of AI video over text and what it will take to build a company that can bundle the entire enterprise video value chain in one platform.”
“I’ve met many founders who do not understand how investors think,” he added. “VCs look for companies that will return their investment with interest, so as an entrepreneur you need to communicate that you can be a good fund returner – either by creating and owning a new market or by disrupting an existing one.”
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What makes a winning pitch deck
There are a few hallmarks of successful pitch decks which can help you unlock funding for your business. Here are 5 top tips from Chapman and Riparbelli:
1. Tell a compelling story
At the growth stage, you need a healthy balance of story, vision and business metrics. Don’t just talk about the product but also explain the problem it solves, the scale of the opportunity and the go-to-market strategy.
2. Put your customer first
When outlining the value proposition, focus on why customers care enough to pay for your solution. Discuss the size of the market opportunity, your target customers and how you reach them.
3. Keep it simple
Stay simple and concise. Focus mostly on the product and customers initially, and save the
technology deep-dives for later on in the process.
4. Spotlight your team
Ultimately, it’s the people who will make the business a success and investors are always keen to know about your skills, experience and motivations.
5. Understand the power law
In VC, a small number of investments tend to generate the majority of the returns, known as the power law. This means that every investment has to have the potential for exponential growth. So highlight your unique value proposition, the scalability of your product and the size of the market opportunity.
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How to close more deals smarter and faster.


