The Twenty Minute VCAydin Senkut: How I Scaled from a $4M Angel Fund to $900M AUM | 20VC #890
CHAPTERS
- 0:00 – 3:46
From Google operator to founding Felicis: outsider path into venture
Aydin recounts his early fascination with investing, his entrepreneurial family background, and the pivotal decision to leave Google after seeing hypergrowth firsthand. He explains how angel investing became the bridge to creating Felicis, especially after failing to land a job at established VC firms.
- •Grew up around entrepreneurship and investing in high-inflation Turkey
- •Left Google seeking a more entrepreneurial, from-scratch journey
- •Started as an angel investor, then evolved into building a venture firm
- •Being denied VC jobs pushed him to start Felicis rather than apprentice
- •Positioned himself as an outsider willing to do things differently
- 3:46 – 5:51
Angel-to-VC mindset shift: building a franchise and avoiding the ‘bucket’ trap
The conversation shifts to how Aydin’s mentality changed when deploying other people’s capital. He emphasizes team-building, broad strategy across stages/geographies, and deliberately avoiding crowded, orthodox positioning even when it complicates fundraising.
- •Moved to VC to build a team and an enduring firm, not just invest solo
- •Belief in a single universe of great companies across stages and geos
- •Capital/time/resource constraints make angels less able to pursue that strategy
- •Early Felicis intentionally did non-orthodox deals (e.g., international, later-stage)
- •Copying incumbents is a losing strategy in competitive venture markets
- 5:51 – 7:26
Fund I fundraising reality: ‘no bucket’ positioning and LP empathy
Aydin describes the difficulty of raising the first Felicis fund due to his unorthodox strategy and non-traditional background. He highlights the value of experiencing fundraising firsthand to build empathy for founders and to understand firm-building mechanics.
- •First fund positioning made categorization difficult for LPs
- •Rejection in LP conversations mirrored founder fundraising pain
- •Closing Fund I required hustle and a few believers taking a chance
- •VC fundraising is a core skill for franchise building, not optional overhead
- •Understanding how hard capital is to raise informs deployment discipline
- 7:26 – 10:56
Making sense of ‘crazy’ early-stage pricing: inflation, constraints, and upside focus
Aydin reframes today’s high valuations by anchoring them to long-term inflation and cost-of-living shifts. He argues that investors have limited levers (deal count, ownership, or price), so Felicis optimizes primarily for access to the best companies and maximal upside.
- •Nominal valuations look shocking but are less extreme after compounding/inflation math
- •Investors must adapt: fewer deals, less ownership, or accept higher entry prices
- •Felicis prioritizes being in the best companies over optimizing entry terms
- •Great companies often become 10–20x larger than expected, dwarfing entry-price differences
- •Unlimited upside is the most important variable in venture outcomes
- 10:56 – 12:49
Ownership on the first check: fund-size math, flexibility, and earning the right to double down
They dig into when first-check ownership matters and when it can be treated as a strategic entry point. Aydin explains how Felicis uses fund models to target ranges, sometimes entering small and scaling ownership later by demonstrating value to founders.
- •Ownership targets should be driven by fund size and a deployment model
- •First-check ownership matters, but access sometimes requires smaller initial checks
- •Felicis uses “strategic” entries and increases stake over time
- •Doubling/tripling down works when the firm proves value to founders
- •Speed and flexibility are key advantages, especially for newer franchises
- 12:49 – 15:08
Deployment pace compression and diversification across time, sectors, and geographies
Aydin responds to faster fund deployment cycles by emphasizing antifragility and the need to be ready for regime changes. He shares LP board guidance on vintage diversification and outlines Felicis’ preference for broader diversification and a larger portfolio size.
- •Modern funds can deploy in ~12 months versus multi-year pacing historically
- •LP board advice: stay active but maintain vintage diversification
- •Stage-mix adjustments can extend deployment without losing speed
- •Felicis favors broader diversification vs. highly concentrated approaches
- •Belief that 40–50 companies per fund is more realistic than 20 in venture
- 15:08 – 17:34
Scaling portfolio support while leading: fund models, team growth, and adapting to 2021 extremes
Harry challenges the feasibility of leading many companies; Aydin explains that firm growth must match market growth. He details how Felicis uses a model-driven plan to determine fund size and maintain the capacity to lead, especially when round sizes spike unexpectedly.
- •To keep leading, firms must scale team and capital base alongside the market
- •Felicis grew from $41M to a $900M fund family to transcend stages and lead more
- •Fund sizing is model-driven, not just based on LP demand
- •Round-size inflation can break plans quickly; funds need buffers and adaptability
- •Smaller funds face harder trade-offs when pricing and round sizes jump
- 17:34 – 21:37
Crossover funds in a crash: public-market realities, ‘signal’ dependence, and edge in originality
Aydin analyzes what market turbulence means for Tiger/hedge funds and why early-stage investing is structurally different from public markets. He argues their strengths are in fast-following with high signal, while original strategy and low-signal decision-making remain a venture edge.
- •Public markets are hard; last decade’s simple alpha trade was ‘long tech’
- •Crossover funds move private to access the best companies beyond public listings
- •Earlier-stage requires making decisions with little signal—unlike Bloomberg-driven publics
- •Crossover strength: fast-follow once high-signal investors/companies emerge
- •Felicis’ edge: original thinking about where the world is going and sector selection
- 21:37 – 24:38
Will crossovers inflate early-stage prices? Founder incentives, non-price value, and operational pattern recognition
Harry worries crossovers will push earlier and inflate Series A pricing; Aydin offers counterpoints. He notes crossovers often cluster in enterprise software and rely on data availability, while founders increasingly recognize that high valuations bring pressure—so coaching and operational experience can win deals.
- •Crossovers’ impact may be narrower due to sector focus (often enterprise)
- •Data-driven approaches struggle at seed/stealth where signal is scarce
- •High valuation can be a double-edged sword—founders must grow into it
- •Early-stage founders often value strategy/coaching and ‘seeing around corners’
- •Operational scars (Google growth, Silicon Graphics collapse) inform better guidance
- 24:38 – 27:47
What Aydin wishes he knew: from solo to team to ‘team of teams’ and hiring for growth mindset
Aydin describes the evolution stages of building a firm and what surprised him most: people decisions. He explains why culture, mindset, and growth orientation are critical, arguing that selecting and developing the right team is harder than picking companies.
- •Lifecycle: solo operator → team → team of teams
- •Early exits provided validation that his angel strategy wasn’t ‘pipe smoke’
- •Hiring: talent isn’t enough—culture fit and growth mindset are decisive
- •‘Picking people is 100x harder than picking companies’
- •Taking non-obvious chances on people can produce outsized outcomes
- 27:47 – 29:28
Felicis’ guiding principle: ‘success with empathy’ vs performance-at-all-costs
Aydin articulates Felicis’ core philosophy: achieving top performance while maintaining empathy in relationships and internal dynamics. He argues that empathy doesn’t mean softness, but rather reducing energy-dissipating conflict so the team can focus on finding and building great companies.
- •Guiding principle: success with empathy (not Kumbaya, but human-centered)
- •Belief that performance and empathy can coexist despite industry skepticism
- •LP support is the ultimate validation of whether the model works
- •Performance-at-all-costs can create internal conflict and wasted energy
- •Aim to channel effort into company-building rather than internal battles
- 29:28 – 32:38
New ‘products’ and the fund-of-funds effort: expanding shots on goal and paying it forward
Aydin reframes product expansion as gaining the ability to invest across the field—more shots, from more positions—while staying true to a global, stage-agnostic strategy. He explains why Felicis built a fund-of-funds effort to partner with complementary managers, extend reach without becoming a 100-person firm, and provide the mentorship he lacked.
- •Doesn’t view stage/geo expansion as new products—it's access and shot-taking flexibility
- •Fund size and team increase allow more attempts and broader positioning
- •Fund-of-funds helps reach more companies without losing the firm’s identity
- •Partnership with complementary GPs provides networks money can’t simply buy
- •Motivation includes ‘pay it forward’ mentorship he didn’t receive early on
- 32:38 – 38:13
Mistakes, misses, and decision process: learning from ‘no’s’ and making 100x/1000x bets
Aydin opens up about missed opportunities (notably Airbnb/Uber) and how failure shaped future wins (e.g., finding Adyen). He argues that venture is defined by the companies you say no to, and that the real ‘A game’ is building a differentiated process and portfolio construction that enables bold, high-upside bets.
- •Missed Airbnb/Uber by overthinking risk; later found Adyen partly from that frustration
- •Many Felicis wins came from adversity: losing rounds, coming back, or long-shot hustle
- •Biggest franchise mistakes are often false negatives, not bad yeses
- •Focus on improving process: network gaps, overlooked/overweighted factors
- •Must underwrite upside scenarios and rare outcomes to capture 100x/1000x returns
- 38:13 – 41:32
Taking cash off the table: probabilistic selling, business model predictability, and LP flexibility
They discuss how to manage liquidity from public positions and when to return value to LPs. Aydin emphasizes probabilistic risk/reward, the predictability of recurring revenue models, and sometimes distributing stock (not cash) so LPs can decide based on their own needs.
- •Selling decisions mirror investing: assess upside plus probability-weighted outcomes
- •Recurring revenue businesses can be more predictable than hardware-like growth dynamics
- •Sometimes best compromise is distributing shares instead of selling for cash
- •Hindsight regret is inevitable; LP needs and responsibilities differ
- •Don’t over-optimize financially at the cost of life realities and long-term perspective
- 41:32 – 48:19
Quickfire close: Antifragile, independent thinking, EQ in venture, and a climate biotech bet
In rapid-fire questions, Aydin reiterates key personal beliefs: antifragility, independence, and the importance of EQ in venture outcomes. He also shares Felicis’ desire to scale founder support, a memorable Shopify meeting, and highlights Living Carbon as a recent investment focused on carbon capture via enhanced trees.
- •Favorite book: Antifragile and relevance amid inflation, war, and climate realities
- •Changed mind: relying less on external validation; stronger independent thinking with experience
- •Overlooked venture skill: EQ and relationship-building alongside being right early and alone
- •LP board as ‘mentor’ substitute; chose toughest, most skeptical LPs for governance
- •Recent deal: Living Carbon—biologically enhanced trees to capture more carbon and resist fire
