Podcast Summary: The Investor with Joel Palathinkal

Guest: Jesse Bloom, Senior Associate at Alpha Partners

Date: September 9, 2025
Host: Dr. Joel Palathinkal

Episode Overview

This episode of "The Investor with Joel Palathinkal" features Jesse Bloom, Senior Associate at Alpha Partners. Jesse shares his unconventional path into venture capital, the mental resilience required to break into the industry, and practical advice for others seeking similar roles. The conversation explores Alpha Partners’ unique investment model, the realities of late-stage investing, and Jesse’s personal and professional journey—emphasizing persistence, networking, and authenticity.

Key Discussion Points & Insights

1. Jesse's Atypical Path into Venture Capital

• Background: Jesse began his career at Morgan Stanley Wealth Management with intentions to join his father’s brokerage in New Jersey.
• Turning Point: Dissatisfaction with traditional wealth management led him to business school, aiming for time to reassess his career.
• Breakthrough: An unexpected introduction by his roommate led to a VC internship at Alpha Partners (then Alpha Venture Partners).
• Emotional Moment:
  “I remember getting the call from Brian Smiga. I was in an airport, and I burst into tears, like, into my... My friend's arms. And I can't remember the last time I cried.” (04:19)

2. The Struggle and Importance of Perseverance

• Post-graduation Uncertainty: Jesse navigated months without a job post-business school, refusing to take the easy route of joining his family business.
• Sheer Determination:
  “As long as I have cash to survive... I’m going to give this my shot because I took a job that I didn't love in the first place, and it's not as easy to leave a job and find a new one.” (11:37)
• Job Search Numbers: 92 applications, 13 interviews, 0 offers (eventually returned to Alpha Partners).

3. Networking and Strategic Persistence

• Networking Efforts: Used Affinity CRM to track applications and relationships.
• Impactful Networking:
  “Networking. Which becomes much, much harder as you become further unemployed or you've been out of the business too long because you always feel like you're taking people's time.” (10:02)
• Advice on Persistence:
  “The way I did it was I touched everyone until I could sense that they were getting annoyed with me... but only 92 real applications.” (15:31)

4. How to Add Value and Stand Out

• Portfolio of Cases: Creating a public case repository to reuse and adapt for applications rather than starting anew each time.
• Artifacts in Applications:
  “Every fund right now has like a deal flow funnel. Applicants spend hours and hours searching for deals and writing theses just for them to like, you know, grab. Oh, thank you very much. Maybe, probably not.” (17:59)

5. Alpha Partners’ Unique Investment Model

• Specialization: Fills pro rata rights for early-stage investors who can't maintain ownership in later fundraising rounds.
• The ‘Hot Hand’ Effect:
  “That's really, we have a very interesting model...the most data backed thesis for venture outperformance. And that is the hot hand effect.” (22:23)
• Operational Details: Focus on Series B and later deals, fast execution (about two weeks), and leveraging lead investors' due diligence.

6. Advice for VC Aspirants

• Energy Management:
  “Biding your time and managing your energy is really important. A lot of people don't understand that you can't just sit and apply...each application is requiring more and more.” (16:26)
• Adding Value: Having a deal or a project to share opens doors and provides immediate value to network contacts.
• Practical Application Tips: Start a website, build and reuse cases, and tailor materials to funds' focus areas.

7. Trends, Sectors, and Macroeconomic Outlook

• Sector Agnostic, with Focus: Large e-commerce, SaaS, digital health, ed tech, robotics; exploring biotech and avoiding apparel.
• SPACs (Special Purpose Acquisition Companies):
  “We see a lot of SPAC potential in AI, machine learning, autonomous cars, that kind of stuff where you're not necessarily in the market yet and you need a lot of capital.” (36:27)
• Emerging Areas of Interest: Clean tech and climate tech seen as promising growth areas due to increased private sector involvement.

Notable Quotes & Moments

• “I don't know why anyone would ever want to do anything else, frankly. I'm just constantly surrounded by the smartest people I feel in the world... I am grateful for every day that I'm in the business.” — Jesse Bloom (07:23)
• “My dad says that you never know who's going to change your life. And that happened to me.” (38:52)
• “The only way in Venture that you get in is someone goes to bat for you again and again and again. And that's how you stay in the game.” (40:59)
• “Our business, it's our niche... People are willing to pay us management fees and carried interest to do this business for them because we've shown that we have the access and we have the operation.” (31:26)
• On overcoming setbacks: “I'd probably be working for my father and I'd be very sad because I feel like I'd be pulling an Eric Trump.” (52:04)

Key Timestamps for Important Segments

| Time | Segment | Description | |--------|------------------------------------|------------------------------------------------| | 02:00 | Jesse’s background & origin story | Joining Morgan Stanley and transition to VC. | | 04:19 | First VC internship breakthrough | Emotional reaction to VC offer. | | 09:09 | Job search–persistence and stats | Numbers on applications, persistence advice. | | 15:31 | Networking vs. being persistent | Striking the balance in networking. | | 22:18 | Explaining the Alpha model | How Alpha finds its niche in late stage VC. | | 34:26 | Macro trends and advice | Sectors to watch, advice for breaking into VC. | | 44:54 | Data on the “hot hand” effect | Academic research supporting strategy. | | 38:52 | Most valuable advice/mentor lesson | The power of unexpected advocates & mentors. | | 53:25 | Practical interview tips | Strategies for handling VC interview processes. |

Q&A Highlights

• Hot Hand Strategy and Data (44:54): Jesse references studies (e.g., Kaplan et al. 2020) supporting performance persistence in top-quartile venture funds.
• Alternative Strategies for Non-Leading VC Funds (48:05): Besides the hot hand, he notes board involvement and classic stock-picking, but highlights the difficulty and time requirement.
• Networking Tactics (59:20): Using “school project” as a reason for outreach or offering to present deals/research of mutual interest.

Memorable, Human Moments

• Jesse’s candid retelling of his emotional ups and downs, relying on a support system, and sharing his own struggles with pride and self-doubt humanize the VC journey far beyond just career tips.
• His willingness to help others, and his particular gratitude to those who helped him during his job search, echo the importance of “paying it forward” in the venture community.

Takeaways for Aspiring VC Professionals

• Persistence, strategic networking, and authentic value-adding are the pillars for breaking into venture capital.
• Finding unique ways to demonstrate your expertise and create artifacts (e.g., investment theses, deal sourcing, blogs) are now table stakes.
• Industry models are evolving, and those able to identify and exploit a unique niche—like Alpha’s pro-rata execution—can differentiate and thrive.
• Personal connections, serendipity, and readiness to capitalize on “luck” are as critical as technical knowledge or quantitative skills.
• Pay it forward: Today's favor is tomorrow's opportunity.

For more, visit the podcast website or connect with Jesse Bloom for advice and networking.