Chapters 8 through 10 of Angel by Jason Calacanis gave me a refreshing and powerful shift in perspective as an aspiring entrepreneur. While the book is primarily about angel investing, these chapters stood out because they emphasized that success in the startup world isn’t solely about having money—it’s about recognizing and leveraging value in all its forms.
In Chapter 8, Calacanis presents practical strategies for those who may not have a large amount of capital but still want to become angel investors. He introduces the concept of investing time, expertise, and connections through advisory roles, syndicates, and networking. This spoke directly to me. As someone who is building my own business, this chapter helped me realize that I shouldn’t only be fixated on raising funds. There is immense power in attracting individuals who understand my vision and are willing to invest their time and knowledge to help bring it to life. Their advice and experience can be just as crucial—if not more so—than a check.
Calacanis also goes in-depth about the cap table and the five kinds of people typically listed on it: founders, employees, advisors, angels, and venture capitalists (VCs). He explains that companies don’t exist without the founder, who starts off owning 100% of the company and usually does the most work over the life of the business. Employees come next in terms of time invested, though their lives aren’t fully tied up in the business the way a founder’s is. Employees usually receive equity through an option pool—options give them the right to buy shares in the future at a lower “strike price,” aligning their motivation with the company’s success. These options typically vest over four years. Advisors, or as Calacanis calls them “the broke angels,” trade their time, skills, and connections for shares in the company. Then come angel investors, who don’t commit their entire lives to one startup but step in early to support founders and help guide them toward professional investors. Lastly, VCs enter once the company has removed a lot of early risk, helping it mature from adolescence to adulthood.
Chapter 9 dives deeper into the role of an advisor. Calacanis shares how his involvement with Dyn led to a $600,000 return—not through investing money, but by offering his expertise. It was a reminder that knowing your value and building your skills can place you in rooms where money isn’t the only currency. As I continue growing as an entrepreneur, I want to surround myself with people who can guide and elevate me—not just financially, but strategically.
Then in Chapter 10, Calacanis reflects on how he wishes he’d started investing right out of college. He encourages young people to challenge the conventional career path and start making bold moves early. While I believe in being wise and discerning, this chapter ignited my interest in learning more about investing now—not later. I don’t have to wait until I’m “established.” I can begin by observing, asking questions, and staying close to the action.
One quote that stuck with me was at the end of Chapter 10: “You can make your own luck in this life by putting yourself next to the people who are already winning.” While I personally believe in the blessings and favor of God rather than luck, I align with the core idea—surrounding yourself with people you aspire to learn from is key. Not to compete with them, but to be inspired, mentored, and equipped.
These chapters not only expanded my definition of investing but also reminded me of the importance of proximity, purpose, and preparation. I’m walking away more open to the idea of angel investing—and more intentional about building the right relationships along the way.
EmpowerMe Life 
Hi Aamiya,
Thanks for sharing this insightful reflection—your takeaways from Angel really highlight how investing is about much more than money. As someone in higher education, I see strong parallels in how we support students and early-stage innovators. Like Calacanis’ “broke angels,” mentors, faculty, and advisors often invest time, expertise, and networks long before financial capital enters the picture.
Your point about building the right relationships hit home. In academia, we focus on cultivating ecosystems where people grow through proximity to those with experience—not just to compete, but to learn, collaborate, and be inspired. That mindset shift from “raising money” to “attracting strategic support” is something we try to instill in our students as well.
The chapters’ call to act early also aligns with what we encourage on campus: don’t wait to be “ready.” Start learning, asking questions, and getting involved now. Like you, I believe purpose, mentorship, and preparation open doors long before traditional investment does.
You’re clearly thinking about business—and relationships—in a very intentional way. Excited to see where that takes you.
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Aamiya, your reflections continue to impress me with both depth and clarity. This post in particular highlights a powerful shift—from seeing investment solely as financial capital to recognizing the immense value in time, expertise, and presence. That’s a mindset most entrepreneurs don’t fully grasp until much later in their journey, and the fact that you’re already embracing it speaks volumes about your leadership.
Your interpretation of the cap table and advisory dynamics was spot on. The way you connected that to your own growth—surrounding yourself with people who elevate your vision, not just fund it—is such a wise and grounded approach. Your mention of building “the right relationships” reminded me that proximity to wisdom often opens more doors than capital ever could.
I also appreciated your reflection on starting now, not later. You’re right—waiting until we’re “established” can delay growth that’s available through observation, preparation, and bold learning today. That balance between faith and strategy you’re cultivating is exactly what will sustain you long term.
Keep leaning into this journey. You’re not just absorbing knowledge—you’re already living it with intention, purpose, and integrity.
Warm regards,
Brent Parker
Owner – Resilience Repurposed LLC
Graduate Student – WCU (M.E.I.L.E. Program)
https://blog.resiliencerepurposed.com
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Aamiya, I enjoyed reading your reflection on Chapters 8-10, particularly your emphasis on the non-monetary forms of value that drive entrepreneurial success. Calacanis’s perspective on leveraging time, expertise, and relationships rather than relying solely on capital is a powerful reminder that the most impactful investments often transcend financial contributions.
The story of Calacanis’s advisory role with Dyn demonstrates how expertise and networks can yield returns comparable to, or even greater than, financial investments. As you mentioned, surrounding oneself with the right mentors and peers can accelerate growth in ways money alone cannot.
Your post has left me pondering how I might apply these lessons, whether through seeking advisory roles or simply being more intentional about the company I keep. Thank you for sharing such a thought-provoking reflection.
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Hi Aamiya,
Your reflection has given me a lot to think about. You are absolutely right that owning a business is more than just the money. I have seen it come up in a few reflections over these past few weeks, but profits are not everything. The relationships small business owners build along the way play a major role on if companies maintain a loyal customer base or not.
I like how the author mentioned ways to invest without investing money. This barter style of mentorship and ownership isn’t something that I have heard a lot about. I think it’s a fantastic way to make investing in a startup accessible to all, no matter how much money or capital a business has. With your business plan, is there any services you would be willing to barter for a specialist to invest time to your cause? With my venture, I am not sure I would have anything I could offer as a non-profit rescue.
Your reflections have always been worth the read throughout this course and I am so glad this last reflection did not disappoint. I hope to see you in a future class and to see your app go live!
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Aamiya, your reflection on Chapter 10’s encouragement to start investing early not just money, but also time and learning is a great call to action. It is easy to feel like you need a certain level of establishment before engaging in the investment world, but observing and asking questions are indeed powerful starting points.
Finally, your interpretation of Calacanis’s quote about “making your own luck” resonates deeply. Whether you attribute it to luck or favor, the core message about the power of proximity to successful individuals is undeniable. Surrounding yourself with those who inspire and can mentor you is paramount. It fosters an environment of continuous learning and growth, which is invaluable in the dynamic startup ecosystem.
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