Grit

The Pull to Build: Joubin Mirzadegan on Grit and Starting Roadrunner

December 8, 2025

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  • Joubin Mirzadegan's career path, marked by intense drive and a desire to prove himself, was shaped by the contrasting influences of his disciplined mother and more permissive father. 
  • The *Grit* podcast was intentionally created as a creative solution for Joubin to build an authentic network of top sales leaders to better advise Kleiner Perkins portfolio companies, mirroring the organic growth of the firm's Portfolio Operations team. 
  • Roadrunner was founded to solve the persistent, career-long pain point Joubin experienced where outdated quote-to-cash software systems could not support modern, complex pricing models emerging from the AI/consumption-based era. 
  • The core problem driving the founding of Roadrunner is the widespread failure of existing CPQ (Configure, Price, Quote) software to handle modern, complex pricing models, a pain point Joubin Mirzadegan confirmed by surveying 35 technology CIOs. 
  • The convergence of massive, persistent pain in the quote-to-cash stack and the emergence of LLMs made the creation of an AI-native CPQ solution, like Roadrunner, a compelling, timely opportunity that required rebuilding the architecture from the ground up. 
  • Joubin Mirzadegan was motivated to start Roadrunner because building an early-stage startup represents the ultimate test of one's character, and he possessed an 'unfair reason to win' due to his deep network of CROs and CIOs and his prior experience scaling complex GTM operations. 

Segments

Roadrunner’s AI CPQ Solution
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(00:00:00)
  • Key Takeaway: Roadrunner is building an AI-native CPQ system to modernize the quote-to-cash stack by using LLMs to structure deals based on historical data and provide real-time benchmarking.
  • Summary: The core business process of delivering a product for money relies on an operating system currently running on old software. Roadrunner aims to fix this by tagging quotes with AI, allowing account executives to structure deals correctly on the fly. This system maximizes commission while ensuring the deal is perfect for the business, putting ‘revenue back in motion.’
Grit Episode Role Reversal
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(00:01:29)
  • Key Takeaway: This special episode of Grit flips the script, featuring host Joubin Mirzadegan as the guest, interviewed by Mamoon Hamid, covering his entire career arc.
  • Summary: For the first time in over 270 episodes, the host is in the guest seat to discuss his transition from sales leader to founder. The discussion covers his time building companies, joining Kleiner Perkins, launching the podcast, and founding Roadrunner. Roadrunner is noted as KP’s first incubation since Glean.
Joubin’s Early Career Path
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(00:02:14)
  • Key Takeaway: Joubin’s early career involved rapid progression through sales roles at cloud security startups (Bracket Computing, Evident IO) before moving to a leadership role at Palo Alto Networks.
  • Summary: Joubin graduated from UC Davis with a BA in international relations and anthropology. His first job was BDR at Bracket Computing, an early cloud security company where he later managed the inside sales team. He then became a top-performing AE and hiring leader at Evident IO before moving to Palo Alto Networks as a central U.S. sales leader, where he built the region into a major ARR engine.
Joining Kleiner Perkins
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(00:03:28)
  • Key Takeaway: Joubin joined Kleiner Perkins as a GTM partner in 2019, driven by an enduring desire to remain close to startups, even experiencing an existential crisis early on about being on the wrong side of the table.
  • Summary: He joined KP in 2019, eventually becoming a partner running portfolio operations, and launched the Grit podcast in 2020 to interview CROs. Despite the role, he felt compelled to be building alongside entrepreneurs, a feeling he shared with Mamoon early in his tenure.
Childhood Influences and Personality
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(00:08:01)
  • Key Takeaway: Joubin’s academic choices were a form of rebellion against his scientist parents, and his dual upbringing fostered a balance between extreme discipline and irreverence.
  • Summary: He chose majors with minimal science to avoid his parents’ scientific focus, graduating early because he couldn’t sit still in classrooms. His mother instilled extreme discipline, while his father fostered irreverence and a willingness to confront situations or do the opposite of what he was told.
Early Hustle and Sales Entry
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(00:04:45)
  • Key Takeaway: Joubin secured his first BDR role at Bracket Computing only after presenting 16 external offer letters to prove his worthiness to the initially hesitant company.
  • Summary: At Bracket Computing, he commuted by biking to the Caltrain station, putting on a blazer, and cold-calling on the train while sweating. He was initially told he was too raw for the BDR role, leading him to collect 16 other job offers before Bracket finally hired him.
Childhood Anxieties and Competition
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(00:10:42)
  • Key Takeaway: Joubin’s childhood was characterized by anxiety stemming from his parents’ divorce and financial instability, fueling a strong competitive spirit and a need to prove himself, especially as the shortest kid in class.
  • Summary: He describes himself as anxious, competitive, and initially rudderless, feeling the need to prove himself due to being short and moving schools. He recalls eating lunch while walking in high school to hide the fact that he was eating alone after moving to San Diego.
Grit Development Through Hardship
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(00:17:06)
  • Key Takeaway: Grit is best developed through consistent effort in activities that genuinely provide energy, and Joubin’s early hardships created a ‘coat of armor’ that fuels his drive.
  • Summary: Joubin believes the unintentional hardships of his upbringing forged an inextinguishable fire within him. He emphasizes that true grit requires consistency over time, which is only sustainable when pursuing things one enjoys and that provide energy. He shared two stories: running into the woods after losing a soccer final and sitting at a piano to figure out how to play it.
First Job Fired and Vaughn’s
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(00:19:35)
  • Key Takeaway: After being fired from Subway for accidentally setting cookies on fire for 30 minutes instead of 30 seconds, Joubin was immediately forced by his mother to resume job searching, leading him to work as a bag boy at Vaughn’s.
  • Summary: His first job at Subway ended when he burned the toaster oven, which was an expensive piece of equipment. His mother insisted he immediately drop off resumes, leading him to Vaughn’s grocery store. He later worked at Vaughn’s to save money for a competition trip, earning $1,000 in tips over two months.
Sales Career Progression
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(00:21:25)
  • Key Takeaway: Joubin aggressively pursued sales roles, driven by a need to prove himself to Bracket Computing, and rapidly advanced from BDR to top enterprise rep by consistently demanding leadership opportunities.
  • Summary: He was fixated on joining Bracket Computing to prove his worth after they initially rejected him. After the company failed to find product-market fit, he joined Evident IO, doubled their logo count in his first quarter, and immediately requested to become a leader instead of remaining an AE. He repeated this pattern at Palo Alto Networks, moving to Chicago to build the Central U.S. business from $100K in renewals to $56M ARR in four quarters.
Chicago Tradition and Podcast Genesis
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(00:28:48)
  • Key Takeaway: Joubin established a weekly standing reservation at the Chicago steakhouse Bivets, which served as an early, informal version of his podcast by providing a consistent venue for deep conversations.
  • Summary: In Chicago, he sought consistency and community, finding it at Bivets, a dimly lit steakhouse. He secured a standing weekly reservation at (6:30) PM every Wednesday with his server, Julio. This practice allowed him to host different people weekly, foreshadowing the structure of the Grit podcast.
KP Portfolio Operations Team
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(00:42:08)
  • Key Takeaway: The Kleiner Perkins Portfolio Operations team was built iteratively, mirroring the podcast’s expansion, by hiring operators at the prime of their careers (Liam, Lauren, Suzanne) to provide tactical and strategic support to founders.
  • Summary: The team expanded from Joubin advising on sales (CROs) to include CMOs, COOs, and eventually CEOs, expanding the scope of support. The team members are ‘dolphins’ capable of oscillating between high-level strategy and deep tactical execution, which is crucial for helping early-stage, technical founders fill go-to-market gaps.
Leverage of Operator Support
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(00:52:27)
  • Key Takeaway: Venture firms can provide real leverage to startups by embedding operators at the prime of their careers, unlike firms that rely on retired executives, which helps founders accelerate from zero to $100M ARR.
  • Summary: Conventional wisdom suggests VCs cannot help startups, but this is true if the support comes from operators who have been out of the game for years. By providing active, prime-career operators as fractional leaders, KP reduces friction and accelerates company momentum. This hands-on support is most impactful in the early innings (Series A stage) before the company matures.
CIO Pain Points and Software Failure
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(00:55:24)
  • Key Takeaway: CIOs uniformly report being criticized by sales leaders because underlying CPQ software cannot handle modern, complex pricing models.
  • Summary: Custom Frankenstein systems built on Salesforce CPQ fail because their underlying data models are inadequate. Pricing models have become complex over 20 years, moving beyond simple seat licenses to consumption-based and varied SKU pricing, which has broken legacy architecture. This situation is compared to the necessary refactoring required when moving from on-premise to the public cloud.
Identifying Investment Opportunity
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(00:57:26)
  • Key Takeaway: The high volume of expressed pain from powerful buyers signaled a clear investment opportunity in the CPQ space, which was validated by the release of GPT 3.5.
  • Summary: Kleiner Perkins became excited by the widespread, intense pain reported by enterprise buying power regarding broken software systems. Initial investigation found no compelling solutions until GPT 3.5 emerged, suggesting LLMs were suited for reasoning over structured and unstructured text like price books and discounts. The subsequent discovery that Salesforce was end-of-lifeing its incumbent CPQ solution abandoned 8,000 customers, creating an immediate market void.
Roadrunner’s Unfair Advantage
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(00:58:45)
  • Key Takeaway: Roadrunner’s path to success was accelerated by the confluence of necessary technology (AI), a complex go-to-market problem, and Joubin’s unique network access.
  • Summary: The problem hadn’t been solved previously because the required technology was absent, and it involved complex distribution channels. Joubin’s role at Kleiner Perkins, managing CIO groups and hosting a podcast interviewing 80 CROs, provided an ‘unfair reason to win’ in addressing this upmarket complexity. He then spent a weekend vibe-coding the initial product, which solidified internal belief in the venture.
Co-founder Recruitment and Team Building
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(01:00:54)
  • Key Takeaway: The core technical risk of Roadrunner—Joubin not being an engineer—was mitigated by recruiting former KP fellows AJ and Eugene, who were independently excited about the CPQ problem.
  • Summary: Roadrunner incorporated 13 weeks prior and immediately secured paid design partners for co-development. AJ and Eugene, who met at Caltech, have extensive experience including building software for the Mars rover and working at Robinhood, Meta, and on an LLM startup. They independently discovered the CPQ pain point, leading them to partner with Joubin, forming what he considers his dream co-founding team.
Motivation for Building
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(01:03:04)
  • Key Takeaway: Joubin felt the ‘itch to go build’ because starting a company is the ultimate test of character, and he realized that every startup journey requires figuring out unique problems step-by-step.
  • Summary: Starting an early-stage startup is viewed as the hardest endeavor, revealing what a person is truly made of. This process is exciting because most founders lack a playbook, forcing them to solve novel problems sequentially. This personal drive, paired with the persistent CPQ problem, fueled his decision to transition from advising to building.
Defining CPQ and AI Application
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(01:05:06)
  • Key Takeaway: CPQ is the beachhead of the quote-to-cash operating system, focusing on configuring products, applying discounts, and managing approvals, which AI can revolutionize by providing instant, intelligent guidance.
  • Summary: Quote-to-cash is the core business process of delivering a product and receiving money, with CPQ being the initial operating system layer. CPQ involves configuring products, managing SKU discounts, and gaining approvals, which is currently done via slow, manual processes involving Deal Desk, RevOps, and Finance. LLMs can act as an omniscient central nervous system, instantly structuring deals correctly for commission, business fit, and approvals, thereby putting ‘revenue back in motion.’
Mission and Hiring Focus
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(01:08:44)
  • Key Takeaway: Roadrunner’s mission is focused on solving meaty, specific problems (like CPQ) to earn the right to build a big company that changes lives through job creation, rather than pursuing overly broad societal missions.
  • Summary: Building a big company is valued because startups fundamentally changed Joubin’s life by providing wealth, responsibility, and community access, allowing him to change others’ lives similarly. Roadrunner is currently hiring, with the primary bottleneck being great engineering talent in San Francisco. The company prioritizes humanizing its team on its website over showcasing customer demand or VC funding.
Defining Grit and Partnership
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(01:11:54)
  • Key Takeaway: Grit is defined as perseverance through sustained effort, exemplified by sticking with the ‘Grit’ podcast despite low industry survival rates, contrasting Joubin’s impatience with Mamoon’s long-term thinking.
  • Summary: Grit means doing something for a very long time, come hell or high water, which is why 99.9% of podcasts fail to last. Joubin views Mamoon Hamid as the longest-term thinker he has ever met, contrasting with his own impatience. This partnership is intended to go the distance over a decade-plus journey, reflecting the time required to build great companies.