The Road To: Building Your Career As an Angel Investor or VC

Building a successful career as an angel investor or venture capitalist (VC) requires more than just financial backing—it’s about developing a strategic approach to sourcing opportunities, evaluating startups, and supporting founders through their growth journeys. Whether you're looking to make your first investment or build a diversified portfolio, the road ahead can be complex, but the right insights can set you up for long-term success.

In this blog, we've curated a collection of on-demand videos that cover essential topics for aspiring angel investors and VCs. From evaluating startups and understanding due diligence to navigating the evolving landscape of corporate venture and scaling your investment firm, these expert-led sessions provide actionable tips, best practices, and real-world examples to help you make smarter decisions.

No matter where you are in your investment career, these videos offer valuable guidance to refine your approach, build your reputation, and increase your chances of success in the ever-changing world of startup investing.

Table of Contents: 

1. FIRE and Desire: Investing 101 for New Angels and Firms

2. Inside an Investor's Mind: Evaluating Startups and Navigating Due Diligence

3. Corporate Venture is the New R&D: Exploring Corporate Funding and Innovation Strategies

4. Smooth Operators: The Secret for Successful Venture Groups

5. Revolution vs. Evolution: Navigating Changing Tech as an Investor

6. The Ones That Got Away: Delivering and Dealing with Bad News About Investment Offers

7. Molding a Horse into a Unicorn: A Hands On Approach for Investors to Scale their Startup

8. Building a Winning Portfolio: Identifying and Refining the Keys to Successful Investments

9. Lightning in a Bottle or Broken Glass: Lessons Learned from Previous Investments

10. Investors without Borders: Does Geography Matter Anymore in Investing?

11. Crowdfunding and Cap Tables: How to Be Successful in the Crowd Investing Space

12. Dealing in Deep Tech: How and When to Invest in Technology that You Don’t Understand

13. Angels and Demons: Sourcing Great Deals and Avoiding Pitfalls in Angel Investing

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FIRE and Desire: Investing 101 for New Angels and Firms

After achieving success through exits or making an impact in previous investment roles, many are drawn to the world of angel investing or starting their own investment firm. Whether you’re flying solo or assembling a team, the path forward can feel unclear.

Topics Covered:

• Defining your market differentiation as an investor

• Attracting high-potential startups to your portfolio

• The role of intellectual property in your firm’s investment strategy

• Key hires to make as you build your firm

Speakers: Richard Dulude, Daniel Acheampong, Betty Francisco, Cvic Innocent 

Inside an Investor's Mind: Evaluating Startups and Navigating Due Diligence

Evaluating startups goes beyond gut feeling—it requires a structured framework and a rigorous due diligence process. In this session, we’ll help you refine your business plan, navigate growth decisions, and manage relationships with investors effectively.

Topics Covered:

• Frameworks for evaluating startups and how they’ve evolved to stay relevant in changing market conditions

• Common types of due diligence and how they vary by company stage, including key areas of focus and potential red flags

• Common reasons startups fail due diligence and where companies typically face challenges in the process

Speakers: Giussepe Stuto, Kleida Martiro, David Fogel, Greg Raiz, Christian Williams

Corporate Venture is the New R&D: Exploring Corporate Funding and Innovation Strategies

Corporate accelerators, venture capital, and innovation strategies are becoming key drivers of startup success and corporate growth. Join us to delve into the evolving role of corporate funding and innovation, and how these elements intersect to shape the future of both startups and established companies.

Topics Covered:

• The differences between corporate accelerators, corporate venture capital (CVC), venture studios, and traditional startup accelerators/incubators

• Strategies for breaking into a career in corporate funding

• The landscape of corporate funds in New England

• How corporate innovation strategies, including CVC and venture arms, help accelerate success for both parent companies and founders

• Knowing when it's the right time for a company to establish a venture arm

Speakers: Alyssa Stapper, Hemanth Kaligotla, Adam L'Italien, Carly Joos

Smooth Operators: The Secret for Successful Venture Groups

The venture capital industry is experiencing a period of hyper-growth, with once lean partnerships now expanding into large organizations that include specialized operators and portfolio services to better support entrepreneurs. As a result, the success of a fund or venture firm is increasingly shaped by both its investment thesis and its ability to engage the right talent behind portfolio companies.

Topics Covered:

• Who are these operators and why are they gaining so much attention in venture capital?

• How to find and connect with operator-investors

• Building your own reputation as an operator-investor

• Targeting and executing strategic priorities in a venture group

• This session is ideal for venture capitalist firms, incubators, solo capitalists, corporate spin-offs, first-time fund managers, and anyone interested in becoming an Operator-Investor.

Speakers: Madison Sowards, Sophie Panarese, David Chang, Julian Chu, Jodi Collier

Revolution vs. Evolution: Navigating Changing Tech as an Investor

The tech industry is constantly evolving, and for investors, adapting to these shifts is crucial. Understanding how to adjust your investment strategies in this dynamic landscape can make all the difference.

Topics Covered:

• Emerging trends in traditional tech-based business models

• How market conditions influence decisions on which industries or teams to fund

• How market conditions affect the way you structure and offer funds

• The profitability of funds in the current market: Is it becoming easier or harder to manage and allocate funds effectively?

Speakers: Priya Yadhav, Renata Merino, Lily Lyman, Mark Crane

The Ones That Got Away: Delivering and Dealing with Bad News About Investment Offers

In the investment world, finding the right fit between founders and investors can be a delicate process. While it’s common to hear about startups seeking funding, there are also times when a startup decides to pass on an investment offer.

Topics Covered:

• Reasons why founders or startups may decline an investment offer

• What investors should do if a startup rejects their offer

• Why an investor might decide to pass on a particular founder, team, or startup

• Best practices for saying “no” to a team of founders

• Recommended follow-up steps after an offer is accepted or rejected

• Identifying the terms that create mutual wins for both parties

Speakers: Howard Kaplan, Fernando Moran Eserski, Raghav Gupta, Jean Hammond, Abigail Risse

Molding a Horse into a Unicorn: A Hands On Approach for Investors to Scale their Startup

Investor capital can provide the liquidity needed for a startup to scale, but money alone won’t solve cash burn or product-market fit issues. The role of an investor goes far beyond the financial contribution—it’s about having a sense of urgency and understanding how to actively support the startup’s growth.

Topics Covered:

• Identifying the specific needs of startups in your portfolio

• Tackling common organizational challenges during startup formation

• Defining the right balance of relationships with founders and the board

• Knowing when and how to intervene in business decisions

• Collaborating with other financing channels to support a portfolio company’s success

Speakers: Adam Kerr, Joe Caruso, John Landry, Gayatri Sarka, Lily Macomber 

Building a Winning Portfolio: Identifying and Refining the Keys to Successful Investments

As the startup ecosystem continues to grow, so does the competition among investors. With increasing deal volumes and sizes, it’s crucial to maintain strong foundational processes that keep your portfolio relevant and successful.

Topics Covered:

• Adjusting your investments to align with current market trends

• How to improve your term sheets for better deals

• Balancing risk management with profitability

• Effective strategies for segmenting and diversifying your portfolio

• Tools to help track and analyze your investments

• The link between good negotiation and a successful portfolio

Speakers: Ari Fine Glantz, Rudina Seseri, Payal Divakaran, George Le 

Lightning in a Bottle or Broken Glass: Lessons Learned from Previous Investments

Investments can lead to varying degrees of success—some anticipated, others not. But whether you encounter failure or success, both offer valuable lessons on avoiding mistakes and improving for the future.

Topics Covered:

• What repeated failures have taught you about investing

• Knowing when it’s the right time to launch a new fund

• The role of intellectual property in startup success

• Recognizing when it’s time for angels to cut ties

• Key rules and challenges to expect when networking with other investors

Speakers: Paul English, Emily Batt 

Investors without Borders: Does Geography Matter Anymore in Investing?

Historically, cities like Boston, New York, Seattle, and Silicon Valley have dominated the venture capital landscape. But in today’s hyper-connected world—especially post-COVID—how much does geography still influence investment decisions?

Topics Covered:

• How much weight investors give to geography when building their portfolios

• Strategies for building trust and rapport with founders remotely

• The role of regions: Are New England investors expanding to new geographies?

• What Boston’s future looks like as an innovation hub in a globalized market

Speakers: Ian Cain, Michael Skok, Lucia Maffei, Daniel Acheampong, Rob Go  

Crowdfunding and Cap Tables: How to Be Successful in the Crowd Investing Space

Startup investing is no longer exclusive to wealthy angels, funds, and firms. Platforms like Kickstarter and Indiegogo have opened the doors for anyone with an internet connection to support the next big idea. But how does crowdfunding fit into the larger funding ecosystem, and what should you know to succeed in this evolving space?

Topics Covered:

• Trends in crowdfunding and what the future holds for the sector

• Benefits and challenges of raising funds through the crowd

• How venture capitalists view startups with crowd-funded money on their cap tables

• Skills and strategies to succeed as a crowd investor, and how they differ from traditional VC investing

• Why some VCs encourage non-accredited investors to “crowd” invest alongside them

Speakers: Chris Lustrino, Aman Advani, Eric Cox, Ashley Olafsen, Yemisi Olorunwunmi

Dealing in Deep Tech: How and When to Invest in Technology that You Don’t Understand

Investing in deep tech often means betting on the unknown. Imagine being presented with blockchain and Bitcoin in 2011—how would you have wrapped your head around those concepts to see the potential of a company like Coinbase? Deep tech requires a unique mindset to evaluate the risks and rewards of cutting-edge innovation.

Topics Covered:

• Identifying when it’s wise—and when it’s not—to invest in unfamiliar tech

• Strategies for bridging the knowledge gap before making an investment

• Evaluating opportunities in deep tech, where challenges are immense, and success may be years away

• Understanding how to assess risk and reward in areas like AI, blockchain, and quantum computing

Speakers: Vanessa Chan, Jason Allen, Michael Kearney, Habib Haddad, Sarah Sclarsic, Dana Attar

Angels and Demons: Sourcing Great Deals and Avoiding Pitfalls in Angel Investing

Diving into angel investing can be exciting, but it comes with its own set of challenges and opportunities. Whether you’re transitioning from larger funding rounds, leveraging your entrepreneurial background, or simply exploring ways to support Boston’s talent, understanding the basics is crucial.

Topics Covered:

• Sourcing high-quality angel investment opportunities

• Adding meaningful value to the companies you invest in

• Common pitfalls to avoid as an angel investor

• Expectations between founders and investors: What should each side ask for?

• Staying involved as companies grow and raise future rounds

Speakers: Samer Yousif, Raj Aggarwal, Firas Raouf, Betty Francisco, Debi Kleiman  

As you embark on your journey to build a career as an angel investor or VC, applying the right strategies, frameworks, and insights is crucial to making informed investment decisions and fostering startup success. The videos in this series provide expert advice to help you navigate the intricacies of startup evaluation, due diligence, corporate funding, and portfolio management.

Keep refining your approach, leveraging these lessons, and overcoming challenges with confidence to grow your investment portfolio. To stay informed on the latest trends, best practices, and resources in angel investing and venture capital, be sure to subscribe to our newsletter below.