I Tried Angel Investing (and It Didn’t Go Well)

High-growth investment opportunities often arise from innovative strategies tailored to private markets. Investors interested in sectors such as technology investment, healthcare investment, and sustainable investment can benefit from expert insights on raising capital for business and understanding venture capital landscapes. 


Gregory Shepard, a veteran entrepreneur and author, shares his journey of building and scaling businesses, offering practical advice for those looking to succeed in the startup world. From overcoming personal challenges to leveraging the right strategies, Gregory’s approach focuses on long-term wealth-building and how to navigate the complexities of private market investments.


Meet Gregory Shepard
Gregory Shepard is the founder of BOSS Capital Partners and founder and CEO of Startup Science. With 12 successful business exits, multiple private equity awards, and extensive experience in scaling businesses, Gregory empowers founders with tools for achieving sustainable growth. Learn more about his methodology and insights at https://gregoryshepard.com/ and explore Startup Science at https://startupscience.io/. Connect with Gregory on LinkedIn: https://www.linkedin.com/in/gregshepard/


Timestamps:
0:32 – Gregory Shepard’s Background: Entrepreneurial Journey
2:18 – Challenges of the Startup World: Mindset, Grit, and Determination
3:57 – Raising Capital: The Hardest Part of Startups
9:04 – Taking on Bigger Projects: Growing with Confidence
12:16 – Overcoming Challenges: Setting High Personal Goals
15:56 – The Entrepreneurial Mindset: Handling Failure and Discomfort
18:10 – Building Resilience: Pushing Boundaries for Growth
25:02 – Raising Capital: Facing Rejection and Moving Forward
28:01 – The Role of Struggle in Entrepreneurship: Importance of Resilience
32:10 – Bad Advice from Mentors, Investors, and Founders: How to Filter
36:40 – Listening to Yourself: The Key to Navigating Advice
40:44 – Market Feedback vs. Opinions: How to Qualify Criticism
42:19 – How to Access Gregory’s Book and Startup Science Platform


Join Angel Investors Network
Ready to unlock exclusive investment opportunities and join a community of successful investors? Join Angel Investors Network today and gain access to cutting-edge startups, high-growth ventures, and expert resources to help you succeed:
https://angelinvestorsnetwork.com/membership/


Discover More from Angel Investors Network
Explore Investment Opportunities: Discover innovative startups and tailored investment opportunities on the Angel Investors Network Marketplace. Connect with ventures that align with your investment strategy: https://invest.angelinvestorsnetwork.com/marketplace
Attend Events: Attend our upcoming seminars focused on business growth, raising capital, and more. Learn directly from industry experts: https://angelinvestorsnetwork.com/events
Take the Capital Raising Quiz: Are you ready to raise capital for your business? Take this free quiz to find out: https://angelinvestor.scoreapp.com
Try the Angel Investing Quiz: Unsure if angel investing is right for you? Take this quick quiz and see where you stand: https://angelinvestors.scoreapp.com


Connect with Angel Investors Network
• YouTube: https://www.youtube.com/@angelinvestorsnetwork
• Facebook: https://www.facebook.com/AngelInvestorsNetwork/
• Instagram: https://www.instagram.com/angel_investors_network/
• Twitter: https://twitter.com/AngelInvestNtwk
• TikTok: https://www.tiktok.com/@angelinvestorsnetwork
• LinkedIn: https://www.linkedin.com/company/angelinvestornetwork/
• Jeff Barnes LinkedIn: https://www.linkedin.com/in/jeffpbarnes/


#AngelInvesting #WealthBuilding #InvestmentOpportunities #PrivateMarketInvestments #HighGrowthInvestment #VentureCapitalInsights #RaisingCapital #Entrepreneurship #TechnologyInvestment #HealthcareInvestment #SustainableInvestment #BusinessSyndication #HighNetWorthInvesting #EarlyStageInvestment #VentureCapitalForEntrepreneurs #InvestingInStartups #BusinessGrowth #AlternativeInvesting

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John Reighard, Partner & EVP

John Reighard is a Partner at Angel Investors Network, where he leverages his expertise in business development, networking, and investor relations to help entrepreneurs secure funding and scale their businesses. With a passion for connecting people and ideas, John plays a pivotal role in fostering strategic partnerships and guiding business owners toward sustainable success. In addition to his work with Angel Investors Network, he also owns and operates two other small businesses.

 

A Connector and Networking Extraordinaire, Business Coach/Consultant, and Inspirational Speaker, John is deeply committed to helping individuals and businesses achieve meaningful results. His mission is to empower entrepreneurs and leaders to create lasting impact through strategic growth, financial acumen, and powerful relationship-building.

 

John has trained with, been mentored by, and provided consulting services to some of the world’s top thought leaders in personal development and business transformation, including Jack Canfield (America’s #1 Success Coach and Founder of Chicken Soup for the Soul), Stephen Covey, T. Harv Eker, Bob Proctor, Blair Singer, Robert Kiyosaki, Neil Rackham, Marcia Wieder, and Roger (Bud) Seith. These experiences have shaped his ability to guide clients through personal and professional growth, helping them unlock their full potential.

 

Before joining Angel Investors Network, John took a sabbatical in 2002, living with his family in Norway, Portugal, and France—an enriching experience that followed 15 award-winning years in Silicon Valley. During his time in the tech industry, he worked for leading companies such as Lucent Technologies, Exodus Communications, Octel Communications, and Brady Corporation.

Meet Jeff Barnes

Jeff Barnes is a former US Navy Nuclear power plant operator on a Submarine, Navy diver, risk management director, technology enthusiast, business growth expert, advisor and management consultant. Mr. Barnes sits on the boards of startup companies, runs a venture fund, supports non-profits supporting military vets, and spends most of his time helping CEOs and founders of growing companies automate, systemize, and scale to 8 and 9-figure valuations.

 

With over 20 years of technology, systems, operations, and marketing experience, Mr. Barnes has advised over 1,000 companies, invested tens of millions in advertising campaigns, and helped companies generate over $1 billion in investment capital.

 

As the chairman of Angel Investors Network and founder of Digital Evolution Marketing Group, Mr. Barnes has worked with founders, entrepreneurs, and CEOs around the world to accelerate the growth of their businesses and achieve substantial exits. He’s a father, husband, veteran, business owner, advisor, and mentor, and his true passion in life his helping others achieve success, freedom, and autonomy in theirs.