Aug 17, 2019 · 43m · neon-show
100xEntrepreneur | Episode 7 | Rehan Yar Khan, Managing Partner, Orios Venture Partners
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 100xEntrepreneur, host Siddharth Ahluwalia interviews Rehan Yar Khan, founder and Managing Partner of Orios Venture Partners, about his transition from entrepreneur to leading venture capitalist, the core criteria behind building enduring companies, and the macroeconomic impact of India's startup ecosystem.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Siddhartha as informed peer 2.6 Guest teaching 3.1 Guest disagreement 0.6 Siddhartha pushing back 0.2
speaking balance: gold is Siddhartha, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 8:05 Calling Out Bureaucratic Fear of Startups
Rehan forcefully criticizes government regulators for wanting startup growth on paper while aggressively targeting 20-something founders raising capital out of fear of disruptive economic change.
Hardest push from Siddhartha ▶ 12:28 Pressing for Five Failed ThesesAfter Rehan lists multiple successful investments, Siddharth redirects the conversation firmly to ask for specific examples of failed theses and the learnings derived from them.
Biggest teaching moment ▶ 13:40 Why Home Services Resist ProductizationRehan gives a clear breakdown of why home services aggregation platforms stumble, demonstrating that hyper-customized manual labor cannot be standardized into a repeatable digital product.
Siddhartha holds their own ▶ 32:34 Host Validating Gut Feel from Lack of Early DataSiddharth leverages his own entrepreneurial experience to jump in and complete Rehan's insight, noting that intuition is mandatory early on because founders have no historical data to rely on.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Siddhartha as informed peer | Guest teaching | Guest disagreement | Siddhartha pushing back | Why |
|---|---|---|---|---|---|---|
| Transitioning from Angel Investing to Founding Orios | 2 | 3 | 0 | 0 | Siddharth asks foundational questions about the transition from angel investing to setting up an institutional fund and Orios' long-term purpose. Rehan explains the seed-stage funding gap in India and the economics limiting seed fund AUM size. | |
| Addressing Regulatory Backlash and the Angel Tax Crisis | 3 | 4 | 2 | 0 | Siddharth brings up the angel tax crisis and government scrutiny against startups. Rehan delivers an impassioned critique of bureaucracy fearing rapid innovation and argues that regulation will always lag behind technological progress. | |
| Investment Theses: Winning Bets and Lessons from Failures | 3 | 4 | 0 | 1 | The host asks about successful market theses and then presses Rehan to elaborate on failed investment theses. Rehan analyzes why hyper-local blue-collar home services and luxury commerce failed to scale. | |
| Anti-Portfolio: Reflections on Missed Unicorn Opportunities | 2 | 4 | 1 | 0 | Siddharth asks about anti-portfolio regrets and what distinguishes 100x founders from 2x founders. Rehan shares his missed OYO investment and introduces his core thesis that elite founders possess the thick skin to never take offense. | |
| Evaluating Market Demand and Next Horizon Opportunities | 3 | 3 | 0 | 0 | Siddharth queries whether founders should start in legally and operationally contentious sectors. Rehan responds that massive underlying demand overrides regulatory friction, citing emerging opportunities in India 2, 3, and 4 markets. | |
| Daily Routines, Work-Life Cadence, and Culinary Passions | 1 | 1 | 0 | 0 | A relaxed personal lifestyle discussion where Siddharth asks about daily habits. Rehan shares his night-owl routine, handling morning WhatsApp backlogs, and running two distinct gourmet dining clubs. | |
| Personal Mindsets, Pragmatism, and Essential Reading | 2 | 2 | 0 | 0 | The host inquires about psychological mindsets and reading lists. Rehan outlines his balanced view on health, business, and personal life, recommending Blitzscaling and Shoe Dog. | |
| Overcoming Early Struggles and Orios' Value Proposition | 4 | 3 | 1 | 1 | Siddharth prompts Rehan on personal vulnerability and Orios' fund identity. Rehan recounts raising fund one without a finance background and explains how founder intuition trumps data, prompting a brief collaborative peer exchange. | |
| Investment Criteria, Tech Competence, and Unconventional Mentors | 3 | 4 | 1 | 0 | Siddharth asks about the quantitative checklist Orios uses to write checks and Rehan's life mentors. Rehan explains their conversion funnels, insisting on in-house tech competence and reframing mentorship to include books, peers, and family. |
Statements from this episode (18)
Khan: Ola was funded before Uber existed; it was not a copycat
“I was the first investor in Ola. Very interesting investment in Ola. A lot of people don't know this, but, ah, the Ola investment was actually a pre Uber investment. Uber didn't actually exist when we invested in Ola. So, a lot of people always think Ola was a…”
Khan: Angels funded multiple rounds for Ola and Druva before VCs entered
“Very often when we invest in companies, including Ola and Druva, right? We had to do multiple rounds of funding before the next round of investors would come in.”
Khan: Seed funds will never become very large in AUM
“So we are a seed fund and seed funds, as you know, will never become very large in AUM. Some of the most successful seed funds in America are yet 152 hundred million dollars, two hundred and fifty million dollars at most.”
Khan: Flipkart has created more millionaires than Infosys
“You've got companies like Flipkart, which have created more millionaires than Infosys has created, for example.”
Khan: Startups are now India's largest job-creating industry
“And certainly if you look at the last 12 years in 2008 is when the venture capital revolution started in India. This is the largest job creating industry in India. It's no longer IT services or banking or something like that. It's the startup industry, right?”
Khan: India's luxury and top-end consumer market remains small
“The top end of the market in India, anything to do with luxury has remained small.”
Khan: On-demand home services fail because custom tasks cannot be productized
“We found that that thesis didn't work because you know, each job is such a custom job that you cannot productize it.”
Khan: Passed on OYO after meeting a sleeping 17-year-old Ritesh Agarwal
“So I think OYO was a company I had met Ritesh, and I didn't end up investing. In, in my defense, you know, he was 17 years old, and when I met him, he was sleeping.”
Khan: Passed on investing in Swiggy, Capital Float, and Freshdesk
“Swiggy is another one that, ah, you know, I ended up passing on. Then there was Capital Float. There was, ah, there were so many. There was, ah, Freshdesk.”
Khan: Founders who scale massive businesses do not take offense
“I think the biggest reason, and this may seem like an odd one, is that I feel people who build big businesses or people who are successful in life don't take offense. People who take offense, you know, or something has happened to me, those people get stuck in…”
Khan: Early rival sent thugs with hockey sticks to Ola's office
“There was a cab company in in Bombay, which sent, like, gundas to the office to beat, beat these guys up, and they broke, like you know, they broke, like, glass walls and all with hockey sticks, and these guys stuck it out through that.”
Khan: Early Ola founders faced an FIR for operating illegal services
“Somebody had got an FIR filed against them, against the founders in the RTO for operating illegal services, so they had to deal with that.”
Khan: Prospective investors passed on early Ola, arguing street hailing sufficed
“I remember when I was syndicating the Ola round, and I was trying to get other people into it, and nobody wanted to invest. People were like, yaar, ye kya Bekar company layo, I can wave my arm and get a cab. Right, Bombay. Right, so who's going to order these …”
Khan: Orios reviewed 4,083 pitch decks in 2016 to make four investments
“We looked in 2016, we looked at 4083 power points. We met over a thousand of them to invest in Ford.”
Khan: Ola beat Uber in India by aggregating one million tourist vehicles
“See the reason I think the reason Ola won in India versus Uber, they never, they were never a copy of Uber. It was an original idea. That the OLA team had that there are a million tourist vehicles in India and I can aggregate them.”
Khan: Orios avoids second-time founders due to their high valuation demands
“No, no, we prefer only first time entrepreneurs. We can't afford the valuation of the second time entrepreneurs. They're just too high.”
Khan: Early Dilution Does Not Matter If Founders Build Large Businesses
“So this thing that a lot of founders think, for example, I'll get very diluted or I should, that is not really a concern. Once you build a big business and you're very good at it, you'll be so indispensable that investors will be bending over backwards to give…”
Khan: Founders Are Better Off Raising From Smaller Funds Than Mega-Funds
“So similarly, if you are a founder, and instead of going and raising money from the biggest funds, Or the biggest investors, you're better off targeting smaller investors because you are more important for them. That investment cannot fail for them. Right? Tha…”