The Power of Persistence: Why 100+ Rejections Can Lead to Billion-Dollar Success

By Matt Holland, Founder at BizDealRoom

After helping hundreds of entrepreneurs navigate the treacherous waters of investor relations, I've learned one fundamental truth: rejection isn't the opposite of success—it's often the pathway to it. At BizDealRoom, we see this reality play out daily, and the numbers tell a compelling story that every founder needs to hear.

The Harsh Reality of Fundraising

Let me share some sobering statistics from our experience at BizDealRoom. Our formula shows that, on average, it takes 60 enquiries to connect with one serious investor. That's 59 "no's" for every "yes," and even that "yes" doesn't guarantee funding—it just gets you to the next conversation.

But here's where it gets interesting: I've witnessed founders who've connected with hundreds of potential investors. One project we worked on generated over 400 enquiries, yet the founders still couldn't close the deal. This taught us a crucial lesson that fundamentally changed how we operate.

The Two-Model Approach: Why Success Rates Matter

This experience led us to develop two distinct service models at BizDealRoom:

Model 1: The Independent Route Founders handle their own pitching process after we provide connections. Success rates vary wildly based on the founder's ability to sell their vision.

Model 2: The Partnership Route We work on a retainer basis, actively supporting the entire process from pitch refinement to investor relations. Our success rate here? Above 85%.

The difference isn't just about experience—it's about understanding a fundamental principle that many founders overlook: people invest in people, not just ideas.

The Perfect Package: Great Founder + Great Idea

We've become extremely selective about the deals we take on because we've learned that even the most brilliant idea can fail if the founder isn't "investible." The magic combination we look for is simple:

• A great vendor (business owner) who can articulate their vision, handle rejection professionally, and inspire confidence
• A great product or idea that solves a real problem in a scalable way

Without both elements, even months of effort can lead nowhere. That's why we now spend considerable time evaluating not just the business concept, but the founder's ability to represent it effectively.

Learning from the Giants: Rejection as a Stepping Stone

The most successful entrepreneurs in history have one thing in common: they were told "no" countless times before hearing their first "yes." Let's look at some inspiring examples:

Melanie Perkins - Canva (Australia)

Canva's co-founder has one of the most documented rejection stories in Australian startup history:

• Rejected by over 100 investors while trying to secure funding for what's now a $26-40 billion company
• Lived with her brother for three months in San Francisco, pitching to VCs who all said no
• Eventually met investor Bill Tai at a conference where she wasn't even a scheduled participant
• Even learned windsurfing to improve her networking opportunities at investor retreats
• The key moment came when she refined her pitch to focus on the emotional problem rather than the technical solution

Tim Westergren - Pandora (USA)

The Pandora founder's story is perhaps the most extreme example of persistence:

• 348 unsuccessful funding pitches before his 349th attempt finally succeeded
• Two years of deferred salaries for all employees while chasing investors
• The company that eventually sold for $3.5 billion to SiriusXM

Brian Chesky, Joe Gebbia, Nathan Blecharczyk - Airbnb (USA)

• Rejected by 7 investors in their initial round, with 5 sending formal rejections and 2 not even responding
• Seeking just $150,000 for 10% of what's now a $75+ billion company
• Had to sell cereal boxes themed around presidential candidates to stay afloat

Luke Anear - SafetyCulture (Australia)

• Went to extreme lengths to raise capital, including hosting a "fight night" to make cash
• SafetyCulture is now valued at over $1 billion

Scott Farquhar and Mike Cannon-Brookes - Atlassian (Australia)

• Built their company on $10,000 of credit card debt when traditional VC funding wasn't available
• Atlassian reached a peak market cap of over $100 billion

The Australian Advantage: Persistence in a Challenging Market

Australian founders face unique challenges. As Blackbird Ventures' Niki Scevak noted, while the local VC market has traditionally been limited, "when you are raising $10 million, $20 million, or more, the market is a truly global one."

Despite raising less than US$34 billion in total VC funding since 2000, Australia ranks fifth in the world for decacorn creation, with six companies worth over $10 billion: Canva, Atlassian, Afterpay, Wisetech Global, AirTrunk, and REA Group.

The Psychology of Rejection: Reframing the "No"

Every "no" you receive is actually valuable market research. Here's how to reframe rejection:

1. Each "no" is feedback - Ask investors specifically why they're passing
2. Rejection refines your pitch - Use the feedback to strengthen weak points
3. Pattern recognition - If you're hearing the same concerns repeatedly, address them systematically
4. Market validation - Some rejections reveal market timing issues, not fundamental flaws

Melanie Perkins exemplified this approach: "Every time we were rejected or had tricky questions we'd improve our pitch decks. One of the most important things that we learnt was that to convince investors of our idea they had to be convinced that the problem existed and that the problem affected a lot of people."

When Persistence Becomes Productivity

Here's the crucial distinction: blind persistence without adaptation is just stubbornness. Smart persistence involves:

Continuous Improvement

• Refining your pitch after each rejection
• A/B testing different approaches with different investor types
• Building social proof through customer traction between investor meetings

Strategic Targeting

• Researching investor portfolios and investment theses
• Understanding investor preferences and fund mandates
• Timing your approach based on fund cycles

Building Relationships

• Following up with investors who showed interest but passed
• Maintaining contact with warm prospects over time
• Leveraging introductions and warm connections

The BizDealRoom Formula in Action

Our experience has taught us that successful fundraising follows predictable patterns:

Quality over Quantity While our baseline is 60 enquiries per serious investor connection, the best outcomes come from highly targeted approaches to the right investors at the right time.

Founder Readiness Before we engage, we evaluate whether founders can handle the emotional rollercoaster of fundraising while maintaining focus on business operations.

Timing and Traction The best time to raise money is when you don't desperately need it. Investors want to see momentum, not desperation.

Your Rejection Roadmap

If you're currently facing rejections, consider this your roadmap:

1. Document Every Interaction - Track feedback patterns and objections
2. Set Realistic Expectations - Plan for 60-100+ conversations before finding the right match
3. Maintain Business Focus - Don't let fundraising distract from building your actual business
4. Consider Professional Help - Sometimes an experienced intermediary can dramatically improve your success rate
5. Celebrate Small Wins - Each meaningful conversation is progress, even if it doesn't lead to funding

The Bottom Line

Every entrepreneur who's built something meaningful has faced rejection. The difference between those who succeed and those who quit isn't talent, luck, or even the quality of their idea—it's the ability to hear "no" and keep moving forward with purpose.

At BizDealRoom, we've seen this pattern repeat countless times: the founders who treat rejection as information rather than invalidation are the ones who eventually build the companies that change industries.

Remember Melanie Perkins sleeping on her brother's floor in San Francisco, getting rejected by 100+ investors. Remember Tim Westergren making 348 unsuccessful pitches. Remember the Airbnb founders selling cereal to pay rent.

These aren't cautionary tales—they're blueprints. Every "no" you hear today could be one step closer to your billion-dollar "yes" tomorrow.

The question isn't whether you'll face rejection. The question is: what will you do with it?

Matt Holland is the founder of BizDealRoom, where he helps entrepreneurs navigate the complex world of investor relations and capital raising. With over 85% success rate in their retainer model, BizDealRoom has facilitated well over $1bn in funding between traditional capital and finance. 

Sources: Forbes, AFR, Linkedin, the entrepeneur.com