Practiced Serendipity Deal-Flow System
Build systematic sourcing while staying open to unexpected founder encounters
- Difficulty
- Advanced
- Time to result
- ~ongoing to results
- Steps
- 6
- Confidence
- 96%
Practiced serendipity combines structured deal-flow operations with deliberate openness to unpredictable encounters. The empirical side uses a technology stack, CRM, institutional referrals, outreach to other general partners, and repeated follow-up. The opportunistic side places investors near founders, experienced operators, and communities where new companies may emerge, then enables them to act when a promising introduction appears. Each side corrects the other's weakness: systems prevent chance meetings from being lost, while openness prevents a sourcing model from seeing only what its filters expect. Over time, founders, limited partners, corporations, banks, pension funds, and fellow investors become a compounding referral network. The framework does not manufacture luck; it repeatedly creates conditions in which luck can be recognized and converted into qualified deal flow.
Origin
Extracted from Masters in Business, where Sarria Darabi characterized TMV's sourcing process as both empirical and improvisational.
Core principles
- 01Unexpected opportunities favor investors who are prepared to recognize them
- 02A disciplined sourcing system increases the surface area for luck
- 03Long-standing relationships create legitimate informational advantages
- 04Deal flow should come from multiple independent channels
- 05Networks compound over time and cannot be manufactured overnight
How to run it
- 1
Create the Sourcing Backbone
Set up a CRM and consistent intake process for founders, referrals, institutions, and co-investors. Capture context, relationship history, next actions, and ownership of follow-up.
Pro tip Tag every opportunity by source so channel quality can be measured later.
Watch out A CRM becomes useless when interactions are recorded inconsistently.
- 2
Activate Existing Relationships
Ask limited partners, corporate partners, banks, pension funds, founders, and fellow investors to share relevant opportunities. Make the investment criteria specific enough for them to recognize a fit.
Pro tip Explain the problems, sectors, stages, and founder profiles you understand unusually well.
Watch out Generic requests for deal flow tend to generate noise.
- 3
Increase Serendipity Surface Area
Spend time in buildings, events, campuses, and communities where capable founders and experienced operators naturally gather. Remain receptive to opportunities arriving through unconventional circumstances.
Pro tip Choose environments based on founder density and expertise rather than prestige.
Watch out Networking activity is not valuable unless it creates meaningful conversations and follow-up.
- 4
Capture Unexpected Leads
Enter chance encounters into the same system used for formal referrals. Preserve what made the founder or opportunity noteworthy and schedule a concrete next action.
Pro tip Record the lead immediately while the context is still clear.
Watch out Do not let an exciting personal interaction bypass basic qualification.
- 5
Qualify and Route Quickly
Assess fit, credibility, stage, and urgency, then move suitable opportunities into diligence or refer them to a better-matched investor.
Pro tip Use a short initial screen so unusual opportunities are not rejected by an overly narrow template.
Watch out Speed should not become an excuse for consistently skipping diligence.
- 6
Compound the Network
Provide useful feedback, make appropriate introductions, and maintain relationships even when a deal is not pursued. Review source performance and deepen the channels producing the strongest opportunities.
Pro tip Treat every respectful interaction as a potential long-term node in the network.
Watch out A transactional reputation will eventually reduce both referral volume and quality.
In the wild
TMV seeded Trackstar, a universal API for warehouse management, after its founders happened to live in the same apartment complex as a TMV principal. The encounter was accidental, but the firm had the experience and process needed to recognize and pursue the opportunity.
→ An unplanned local connection became a seed investment rather than a forgotten conversation.
A large organization alerted TMV to an interesting company in Athens and asked whether the firm would invest there. TMV's openness to overlooked geographies allowed the referral to enter its pipeline despite the unconventional location.
→ An institutional relationship surfaced specialized international deal flow.
Common mistakes
Waiting Passively for Luck
Serendipity becomes useful only when deliberate positioning, relationship maintenance, and follow-up systems increase the chances of encountering and capturing opportunities.
Over-Automating the Pipeline
A rigid database and outreach cadence can filter out unconventional founders whose promise becomes visible only through conversation or trusted context.
Treating Relationships as Cronyism
Relationship access should open the door, not replace investment judgment. Apply consistent qualification and conflict controls after an introduction.
Is it for you?
Best for
It is best for investors, accelerators, and ecosystem builders who need a durable pipeline of early-stage opportunities.
Not ideal for
It is not ideal for people seeking an immediate pipeline without investing time in relationships, reputation, and operating discipline.
From the transcript
“Our process is one part empirical and one part cowboy,”
“You have to be open to the serendipity, but you have to be practiced in your approach to deal flow.”
“So for us, that comes down to our tech stack, our CRM, our outreach initiatives to other gps, and also relying on the kindness of…”
From the episode
At the Money: Finding Overlooked Private Investments