How Founders Can Source Optimism even from Rejection
Original art by Chris Johanson

How Founders Can Source Optimism even from Rejection

Fundraising is a rite of passage for most founders. Yet, the road to securing capital is rarely straightforward. It's a difficult process of learning and resilience. Founders must brace themselves for rejections, and effectively managing setbacks is critical. Additionally, they need to draw as much insight as possible when/if feedback is given.

In this post, I'll share some of the hurdles of fundraising while highlighting the importance of maintaining a positive outlook. Through recent conversations with first-time founders currently fundraising, it's evident that while practical advice from investors is undeniably valuable, a simple show of faith can help reignite the intrinsic motivation that drives entrepreneurs.

I'd like to share a personal story about the positive impact of a single encouraging message from a potential investor. As a first-time CEO navigating the challenging fundraising landscape of 2022, Sock's mid-2022 seed round started strong. However, our progress mirrored the industry's shift as market conditions dramatically changed. By late 2022, the FTX collapse significantly impacted the blockchain/fintech sector, leading to increased investor scrutiny and caution from VCs. Overcoming obstacles, we secured funding from an incredible group of investors to develop and launch Sock in 2023 - go check it out!

Like most startups in this space at the time, investor rejections and extended timelines were quite common. Amidst these challenges, I unexpectedly received the following email from an investor that offered a silver lining. Although our product didn't align with their investment thesis, these encouraging words were timely and deeply resonated with me, reigniting a sense of optimism and leaving the door open for potential future collaboration.

A portion of what they wrote:

"I have no doubt of your future success…the last person that struck me the same way as you was when I got to spend time with a young entrepreneur named Alexis Ohanian. Serendipity that our paths would cross. You carry some of the same magic and presence. I hope and trust you and your team will similarly find success and happiness following your star."

This experience underscores a crucial point for entrepreneurs facing a path that seems uncertain - a founder's spirit can often be uplifted by a simple act of faith in their ability to succeed. It's about striking a balance between relying ones intrinsic value and granting yourself permission to acknowledge and internalize validation from others.

"Self-belief is immensely powerful. The most successful people I know believe in themselves almost to the point of delusion. Cultivate this early. As you get more data points that your judgment is good and you can consistently deliver results, trust yourself more." - Sam Altman

Self-belief is paramount, as Sam Altman emphasizes, but never dismiss someone's faith in your potential. It's a valuable datapoint that can reinforce your own conviction and create a positive feedback loop.

When encountering rejection, it doesn't always signal a flawed idea or a lack of potential in the founder(s). It might simply be a question of timing, alignment with the investor's present focus, or an unforeseen change in market conditions.

Nevertheless, here are some positive ways to manage rejection:

  • Embrace optimism: In the case above, an investor recognized a founder/team's potential, even if it wasn't a fit for them. Their belief can help fuel your own.
  • Let every "no" guide you: Each "no" can be a catalyst for change and helps you refine your pitch. Analyze the feedback and look for themes to understand what might not be resonating.
  • Always follow up: Show the investor you're committed, say thank you, and keep the relationship. Investors are more likely to invest in people they know and trust.
  • Manage your expectations: Investor meetings aren't commitments. While multiple meetings suggest progress, there is never a guarantee before signing and wiring are complete.
  • It's not personal: Don't take rejection personally and separate your idea from the feedback. Their decision might not be a reflection on your passion or potential.


Remember, fundraising is supposed to be hard. Really hard. There is an almost infinite matrix of variables at play, you’ll have bad pitches, good ones, the inevitable investor ghosting, and everything in between - it's an unavoidable part of the journey. The key is to maintain optimism, learn, adapt. Persistence is crucial, but there's also wisdom in recognizing when to take a step back from speaking with investors. Even strong pitches might not succeed due to external factors. If financially feasible, consider pausing your raise to refine your idea and gather customer validation. This helps preserve your credibility and demonstrates to current investors that you're adaptable and data-driven.

For those beginning their fundraising journey or navigating rejection, remain resilient and learn from each encounter. Though it may sting, a thoughtful rejection will contain exactly what you need to hear, provided you're open to listening.


Thank you to VCs like Haven Ventures, Designer Fund, and the many angel investors out there who are building a supportive ecosystem where founders feel empowered to chase their dreams.

Founders - If you’ve ever had similar experiences, share your story in the comments!

Ivy C.

B2B Growth Leader | SEO | Digital Marketing | Advisor

10 个月

Thank you for sharing! This hits home for so many of us in Silicon Valley. Maintaining positivity, and spreading that positivity is critical when we face steep challenges. Congrats on raising funds when it was nearly impossible in 2022. That's a huge feat ????

Shreshth Kapoor

Founder of Osiflow Creative Agency ? TED-Ed Speaker ? Leader x Speaker x Strategist ? Top 1% Mentor @ ADPList (Global) ? Top Product Strategy & Vision Voice ? Co-founder of OpenUX Design Coummunity (2k+) | 5.4k followers

10 个月

Inspiring! :)

Jeremy Black

Digital financial services, user data portability, and blockchain.

10 个月

“Let every no guide you” is sage advice.

Arianna Orland

Director @ Meta | Creative Direction, User Experience, Design Systems

10 个月

So much hard earned wisdom in this post. It’s wondeful to hear your POV on how to continue to cultivate optimism.

Andrew Whiteside

Advertising Executive | AI & Data-Driven Creative Strategy | Ex-CRO @ Jampp | Helping Brands Scale

10 个月

Thanks for sharing, Rick ??. As a first-time founder currently navigating the fundraising journey, your story really resonates with me. The encouraging email hit home—it's amazing how a kind word can reignite our motivation and drive. Your insights on managing rejection and staying optimistic are invaluable. Thanks for the inspiration and for sharing your journey with us. Looking forward to seeing your continued success!

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