From 20+ startup failures to $100 million a year success: Noah Kagan’s inspiring story and his advice to young entrepreneurs

In a world where the pressure to have it all figured out is omnipresent, Noah Kagan offers a refreshing perspective: it’s okay to feel lost. Reflecting on his journey, Kagan shares 18 invaluable lessons tailored for young entrepreneurs navigating the tumultuous waters of career uncertainty.

Embrace the Unknown

Noah Kagan’s journey began amidst a sea of conformity, where friends pursued conventional career paths. Feeling adrift, he initially questioned his direction but soon realized that uncertainty was a fertile ground for exploration. He added that the early twenties are a period of self-discovery and urges aspiring entrepreneurs to embrace ambiguity, viewing it as a canvas to paint their unique professional narratives.

“When I was younger, all my friends were becoming accountants, consultants, and bankers… but I knew that wasn’t for me. At the time, I felt lost and confused. But looking back, I was exactly where I needed to be. When you’re in your 20s, you’re not supposed to know exactly what you want to do with your career. Instead of trying to predict your career path, focus on taking daily action,” Kagan notes.

Take Risks

Kagan’s entrepreneurial portfolio boasts a colorful array of ventures, ranging from spectacular failures to resounding successes. Reflecting on his youth, he recognizes that the absence of familial and financial obligations provided him with the freedom to take audacious risks. He encourages young entrepreneurs to leverage this freedom, advocating for a mindset of experimentation and resilience in the face of failure.

“I tried A LOT of businesses when I was young and broke, but I had a lot of time (Everspeed, CollegeUp, HFG Consulting, Entrepreneur27, etc.). Early in your career, you can afford to take more risks because you have fewer obligations. Create your own luck by taking a lot of relentless action. Do free work to get your foot in the door, fly across the country to meet with an investor, Start the crazy business idea with your roommate, and take more swings. You only need ONE to win.”

Network Effect:

His trajectory was significantly shaped by his proactive approach to networking. From humble beginnings organizing small gatherings to rubbing shoulders with industry titans like Tim Ferriss and Ryan Holiday, he underscores the transformative power of community. Kagan advises young entrepreneurs to cultivate meaningful relationships early on, emphasizing the reciprocal nature of networking and the invaluable support it can provide throughout one’s journey.

“When I graduated from UC Berkeley in 2004, I hosted dinners, beer meetups, and conferences…even when I didn’t know anyone. The interesting people I helped at the time, like Ramit Sethi, Tim Ferriss, and Ryan Holiday ended up helping me 15 years down the line. One way to get started right NOW: Ask the smartest people you know, “Who is ONE person I should meet?’ A coffee or Zoom meeting may be the smartest investment you’ll ever make!”

Noah Kagan (in background) + Tim Ferriss at a meetup

Share Your Journey

Noah’s commitment to personal documentation through blogging has yielded multifaceted dividends. Beyond serving as a platform for self-expression, his blog has facilitated connections with like-minded individuals and catalyzed serendipitous opportunities. He encourages aspiring content creators to embark on their own digital odyssey, highlighting the potential for personal growth and professional advancement that comes with sharing one’s journey authentically.

“I’ve been writing on my personal blog since 2000 (!!) It’s led me to connect with amazing people and meet my business partner Chad Boyda. Creating content is a career cheat code. Worst case? You learn how to write and promote your work. Best case? You attract life-changing opportunities. You also get to look back on yourself and appreciate how far you’ve come.”

The Power of Words

Kagan’s foray into copywriting underscores the pivotal role of effective communication in driving business success. Despite initial skepticism, a bold email subject line penned by a friend yielded unprecedented results for his startup, AppSumo. Kagan stresses the importance of crafting compelling narratives that resonate with audiences, emphasizing the art of persuasion and the ability to capture attention in a crowded marketplace.

“When I first started AppSumo, my buddy Neville tried to convince me to let him use “Copywriting” in our emails to help generate more sales. I was skeptical, and for good reason! The first line of the email he wrote was “If you get a boner when I whisper the word ‘Garamond’ into your ear…..you might be interested.” 🙈 But guess what? The day that Neville’s email was sent out was the first-day AppSumo made a $10,000 profit in a single day. Copywriting is not about hitting a word count or writing a five-paragraph essay. It’s about capturing attention and persuading action. You will never be disappointed by improving your communication skills.”

Kagan also shared two great resources to improve your copywriting skills:

• The Boron Letters (It’s free!)
• Neville Medhora’s Copywriting Course

Cold Outreach Mastery

Drawing from his formative years at UC Berkeley, Kagan shares insights into the art of crafting impactful cold emails. He emphasizes the importance of brevity, relevance, and value proposition in capturing the recipient’s attention and eliciting a response. Kagan encourages young entrepreneurs to approach cold outreach as a strategic tool for forging connections and advancing their goals, highlighting the potential for serendipitous encounters and fruitful collaborations.

“I’ve been sending cold emails since I was a freshman at UC Berkeley. The best cold emails: Get to the point, instantly grab attention Answer “What’s in it for me?” If you don’t get a response? Follow up without being rude. If you shoot 100 shots, you’re bound to land one hit.”

Self-Mentorship

Rejecting the traditional mentorship model, Kagan advocates for a proactive approach to self-development. He underscores the iterative nature of growth, urging aspiring entrepreneurs to embrace challenges as opportunities for learning and self-improvement. By soliciting specific feedback and charting their progress, Kagan believes individuals can effectively mentor themselves, bypassing the need for external guidance.

“Wanna know the best way to find a mentor? Become someone worth mentoring. Start things, encounter a problem, ask for SPECIFIC feedback, not advice, and report back on how you did, Repeat 🔁 You’ll realize you never needed a “mentor” in the first place.”

Diversify Income Streams

Kagan’s entrepreneurial journey is punctuated by a diverse array of income streams, ranging from side hustles to full-fledged ventures. He emphasizes the importance of financial independence and resilience, highlighting the value of multiple revenue streams in mitigating risk and fostering long-term sustainability. Kagan encourages young entrepreneurs to explore diverse opportunities, viewing each endeavor as a stepping stone toward greater autonomy and prosperity.

“When I was young, I thought I was special because I started many businesses in college, had a blog, and worked at Facebook. The reality was I was dependent on my boss. Getting fired taught me that EVERYONE is replaceable. One of my first side hustles (freecallsto.com) only made around $50/month BUT taught me the fundamentals of coding and marketing. Start more side hustles. You’ll learn more, earn independent income, and maybe even replace your income to go full-time.”

Prioritize Self-Worth

In a world consumed by external validation, Kagan emphasizes the importance of cultivating self-worth. He urges young entrepreneurs to reject the need for approval from others and instead focus on internal validation and self-fulfillment. By embracing authenticity and self-acceptance, Kagan believes individuals can liberate themselves from the shackles of external expectations, forging their own path to success.

“No amount of money, followers, or acknowledgment will quench your thirst for fulfillment if you don’t learn to be proud of yourself. he truth is the people you’re trying to impress aren’t even thinking about you in the first place. Instead of trying to prove others wrong, prove yourself right.”

Practice Patience

Reflecting on his own journey, Kagan acknowledges the allure of instant gratification and the pitfalls of impatience. He advocates for a balanced approach, urging young entrepreneurs to be persistent in their pursuits while maintaining realistic expectations for progress. By embracing the iterative nature of growth and celebrating small victories along the way, Kagan believes individuals can cultivate a mindset of resilience and long-term success.

“In my 20s, I was impatient to get rich and famous. I beat myself up a ton. That’s a miserable way to live. You don’t have to be so hard on yourself. If you’re doing the reps, the results WILL pay off. Wealth comes from compounded time. Be impatient with actions and patient with results.”

Harness Positive Self-Talk

Noah Kagan candidly shares his struggle with self-doubt and negative self-talk, especially following setbacks like his departure from Facebook. Through years of introspection and growth, he discovered the transformative power of positive affirmations. Kagan advocates for a deliberate practice of balancing self-criticism with self-compassion. He suggests adopting a simple yet powerful habit: for every negative thought, counterbalance it with a positive affirmation. This practice, borrowed from his friend Tynan, serves as a potent tool for cultivating self-confidence and resilience amidst life’s inevitable challenges.

“After getting fired from Facebook, it took years to make peace with the voice in my head. I ignored all the cliche mindset advice because I wasn’t where I wanted to be in life. But as I’ve gotten older and more mature – I’ve realized how powerful your self-confidence matters for your life and business. A practice that’s helped: Any time you say something negative about yourself, also say something positive. (Thanks Tynan for the tip.) You can be your biggest critic as long as you’re also your biggest cheerleader. What’s something nice that you can say to yourself right NOW?”

Avoid Premature Exits

Reflecting on one of his biggest regrets—shutting down CommunityNext prematurely—Kagan imparts a crucial lesson on perseverance. He acknowledges the temptation to abandon endeavors when they lose their initial allure but cautions against succumbing to this impulse too hastily. Instead, Kagan advocates for delegating responsibilities and seeking support when faced with adversity. By entrusting others to carry the torch, entrepreneurs can sustain momentum and foster continuity, potentially unlocking unforeseen opportunities for growth and success.

“One of my biggest regrets is shutting down CommunityNext (my conference business) when I should have hired someone to keep running it. Someone else took that idea, ran with it, and sold it for multiple millions of dollars. Instead of quitting when it gets boring – find someone to run it while you work on the next thing.”

Maintain Work-Life Balance

Despite his relentless work ethic and ambitious pursuits, Kagan emphasizes the importance of striking a balance between professional aspirations and personal well-being including spending time with family and friends and having fun. Recounting his own experiences, he acknowledges the allure of all-consuming dedication to one’s craft, but also recognizes the inherent value of leisure and diverse experiences. Kagan encourages young entrepreneurs to prioritize self-care and exploration, viewing these endeavors not as distractions, but as sources of inspiration and creativity. By nurturing a holistic lifestyle, individuals can cultivate resilience and sustain their passion for entrepreneurship over the long haul.

“I worked A LOT in my 20s. I don’t regret it – because it got me to where I am today. But don’t forget to have fun too! Your youth is about a diversity of experiences. Play sports. Travel abroad. Hang out with friends. Ironically, doing those things will give you more inspiration for your work.”

Seek Career Insight

Noah Kagan advocates for informed decision-making when it comes to career choices. Rather than being swayed by glamorous job titles or external perceptions, he encourages aspiring entrepreneurs to seek firsthand experience and insight into their desired fields. Kagan proposes a proactive approach: reaching out to professionals for shadowing opportunities and informational interviews. By gaining firsthand exposure to the day-to-day realities of various professions, individuals can make more informed decisions about their career paths, ensuring alignment between their passions and professional aspirations.

“I wish I job shadowed and interviewed more people. In school, we’re conditioned to fall in love with job titles, without knowing the day-to-day work. It sounds cool to be a surgeon until you realize you have to deal with blood all day. Here’s a template you can use: “Hey, I’m a Senior at X college interested in [specific field]. Can I see what you do for a day?” Don’t let an impressive-sounding title distract you from what matters most: doing work you enjoy.”

Leverage Your Network

Drawing from his own experiences in the vibrant tech ecosystem of the Bay Area, Kagan underscores the immense value of cultivating a robust network. He acknowledges the role of serendipity in forging meaningful connections but also emphasizes the importance of intentional relationship-building. Kagan encourages individuals to leverage both physical and digital communities to expand their network and access valuable resources. Whether through in-person meetups, online forums, or social media platforms, he believes that nurturing a diverse network of mentors, peers, and collaborators can accelerate personal and professional growth, opening doors to new opportunities and insights.

“Growing up in the bay was a huge cheat code. I was surrounded by talented and driven people. As cliche as it may be, the people in your life DO matter a ton. If you can’t geographically surround yourself with exceptional people, surround yourself digitally. Who’s on your WhatsApp? Text groups? Twitter DMs? And are those people helping you get closer or further from your goals?”

Learn from Biographies

Building on his voracious appetite for knowledge and personal growth, Kagan extols the virtues of learning from the experiences of others. He recommends immersing oneself in biographies of notable figures across various domains, from business titans like Steve Jobs and Bill Gates to spiritual leaders like the Dalai Lama. By studying the successes and failures of these luminaries, Kagan argues, individuals can gain invaluable insights and perspectives that inform their own journey. Biographies serve as a treasure trove of wisdom, offering timeless lessons and actionable strategies for navigating the complexities of life and entrepreneurship.

“A wise friend once told me, “There are million-dollar lessons hidden in $30 books.” Biographies give you a unique peek into the lives of great people. Instead of learning from your own mistakes, why not learn from those who have come before you? Some of my favorites: Steve Jobs, Bill Gates, and Dalai Lama.”

Keep a Journal

Reflecting on his own practice of journaling, Kagan emphasizes the importance of self-reflection and introspection in personal development. He encourages individuals to maintain a private journal, documenting their thoughts, experiences, and emotions as they navigate life’s ups and downs. Beyond serving as a therapeutic outlet, journaling enables individuals to gain clarity, track their progress, and identify patterns of behavior and thought. Kagan suggests viewing journaling as a form of self-coaching, allowing individuals to cultivate self-awareness and resilience in the face of adversity.

“I’ve kept a private blog since my time at Facebook. It’s helped me become aware of my thought process and emotions. Document how you’re thinking about your life as you’re living it. You don’t even need to share it online. Plus, it’s cool to see how your thinking evolves.”

You’re Gonna Be Okay

Noah Kagan concludes his sage advice with a heartfelt reassurance to young entrepreneurs: it’s okay not to have everything figured out. He urges individuals to adopt a broader perspective, recognizing the inherent uncertainty of life’s journey. Amidst the pressures of societal expectations and personal ambitions, Kagan implores individuals to find solace in the present moment, embracing the inherent beauty of life’s unpredictability. By surrounding oneself with optimism, seeking inspiration, and embracing the uncertainty of the human experience, Kagan believes individuals can navigate life’s challenges with grace and resilience, confident in the knowledge that they’re on a path toward fulfillment and success.

“You’re young. It’s okay if you don’t have everything figured out. Zoom out. We’re just a bunch of monkeys floating around on a tiny rock in space. Hang around optimistic people. Do things that inspire you. Enjoy the party while we’re around. It will all work out. 

Rooting for you,

Noah 🌮”