

Venture with Grace
Grace Gong
I host a top VC podcast called Smart Venture Podcast (SVPpro.com). Past guests include C-level/VPs of Google, Meta, Amazon, Sephora, Dunkin' Donuts, Chipotle, Pepsi, Instagram, Deloitte, Reddit, Lyft, etc. Managing Partners of top funds (many were featured on the Forbes Midas List) and unicorn founders (founders of Craigslist, Square, Loom, Cruise, etc.) Venture with Grace is my new spin-off series that features top LPs, GPs, solo GPs, Angel Investors, top AI founders, and other experts in tech and business to cover specific domain expertise.
Watch this Live on LinkedIn/ YouTube: Grace Gong
Watch this Live on LinkedIn/ YouTube: Grace Gong
Episodes
Mentioned books

Feb 1, 2025 • 1h 10min
Lesley Young: Fractional CRO on Growing Vimeo & Sourcegraph
Lesley Young is the fractional CRO of Vimeo and Sourcegraph. She is an LP at Stage 2 Capital. Prior to that, she was the CRO of Gem and VP at Segment. She is a creative, visionary, and decisive leader with a track record of integrating and elevating go-to-market strategies that drive revenue and customer growth while steering through economic uncertainties and growth periods. Combines business and technical acumen to swiftly identify and execute pivotal priorities, fostering new customer acquisition and expansion. Acknowledged for deploying efficient and repeatable growth strategies tailored to specific market segments, consistently surpassing multi-million $ revenue targets, delivering exceptional YoY growth, and ensuring long-term company durability. Track record includes participation in successful IPOs and exits, including $3.2. Billion acquisition of Segment Inc. by Twilio in 2020, the successful 2015 IPO of Box at a valuation of $2.3 billion, and the $1 billion acquisition of MySQL by Sun Microsystems in 2008.
Topics:
The Role of a Fractional CRO
Adapting Growth Strategies Across Different Business Models
Building High-Performance Revenue Teams
#GrowthEndurance #RevOps #GTMStrategy #B2BSaaS #SalesLeadership

Jan 31, 2025 • 1h
Ex-Tableau CFO Damon Fletcher on Making Data-Driven Decisions
Damon Fletcher is the Founder & CEO of Caliper. Caliper transforms cloud cost and usage data into actionable insights with an intuitive analytics platform. Designed for Data Analysts, DevOps, FinOps, IT, and finance professionals, Caliper offers seamless control over cloud environment. Prior to Caliper, Damon was the CFO of DataRobot and Tableau.
Topics:
The Evolution of Cloud Economics
Building Analytics Tools for Multiple Stakeholders
The Future of Data Companies
#CloudCosts #FinOps #StartupCEO #DataAnalytics #TableauAlum

Jan 30, 2025 • 1h 8min
Anurag Chandra: Board Trustee, San Jose Pension Fund
Anurag Chandra is a CIO at a Single Family Office. He has spent 20 years in Silicon Valley as both an investor and an operator. He has helped lead three venture capital funds, managing over $2B in aggregate. Anurag has been a senior executive in three enterprise technology startups, two of which were sold successfully to public companies. He was a partner with Fort Ross Ventures a traditional mid-stage VC firm with strategic ties to Sberbank (Europe’s largest bank). He is also a Trustee for the $2.5B San Jose Federated Employees Retirement Fund and Chairman of its Investment Committee and Vice Chairman of its Joint Personnel Committee.
Topics:
Cross-Border Growth Expertise
Insights from managing the San Jose Federated Employees Retirement Fund
How public market experience influences private market investing
#VentureCapital #Enterprisetech #InternationalInvesting #CrossBorderVC

Jan 30, 2025 • 1h 4min
Josh Stein, Threshold Managing Partner: Box to Twilio - Building Tech Giants
Josh Stein is a co-founder and Managing Partner of Threshold. He currently holds board responsibilities at ChangeEngine, Databook, Inscribe, LaunchDarkly, LendKey, Sanity, and Talkdesk. He is also actively involved with the firm's investments in AngelList, CloudZero, Doximity (NYSE: DOCS), Front, Imbue, and Rippling. His previous investments include Box (NYSE: BOX), Chartbeat (Cuadrilla Capital), Eventful (CBS Local), GoodGuide (UL), iList (IGN/News Corp), Periscope Data (Sisense), Polaris Wireless (strategic recapitalization), Redfin (NASDAQ: RDFN), Selligy (Veeva Systems), SugarCRM (Accel/KKR), Swell (Apple), Tremor Video (NYSE: TRMR), Twilio (NYSE: TWLO), Yammer (Microsoft), and Yardbarker (Fox Sports Interactive).
Josh was a VP at Telephia, where he managed a group providing strategic analysis and information to the nation's largest wireless carrier. Previously, Josh was a co-founder, director, and the chief strategy officer for ViaFone (NYSE: SY), a leading provider of wireless enterprise applications. Josh has also held positions in product management at Microsoft and NetObjects, and was a management consultant in the San Francisco office of The Boston Consulting Group.
Josh holds a BA from Dartmouth College, an MBA from the Stanford University Graduate School of Business, and a graduate of the Kauffman Fellows Program. He currently serves on the board of trustees of the Crystal Springs Uplands School. Previously, he served on the board of directors of the Stanford GSB Trust, the Center for Venture Education, and the Kauffman Fellows Program, the leading educational fellowship in venture capital. Josh was named by Forbes to its annual Midas List of top technology investors for three consecutive years and was twice recognized as a “top VC investor” by New York Times / CB Insights in their annual rankings. He was also a recipient of the Deloitte Fast 500 Venture Capitalist of the Year award.
Topics:
Evolution of Enterprise Software
Boardroom Dynamics and Social Psychology
The Art of the Pivot
#VentureCapital #ThresholdVC #JoshStein #TwilioInvestor

Jan 28, 2025 • 1h 1min
John McMahon: Former Snowflake & MongoDB Board Member, 5X Public CRO
John McMahon, a seasoned expert in scaling sales teams and former board member at Snowflake and MongoDB, shares invaluable insights. He emphasizes the critical importance of identifying decision-makers and understanding customer needs in sales. McMahon discusses the parallels between fundraising and the sales cycle, offering strategies for effective communication and relationship-building. He highlights the role of active listening and innovative storytelling in mastering sales, while also reflecting on the complexities of leadership and balancing personal life as a CRO.

Jan 26, 2025 • 1h 3min
Eventbrite's CMO Samantha Wu on Breaking Barriers in Tech Marketing
As the Chief Marketing Officer for Eventbrite, Samantha Wu leads the strategic direction of the company’s marketing initiatives as it evolves into a consumer destination for event discovery.
Prior to joining Eventbrite, she served as the CMO of Braintrust, the first decentralized talent network where she oversaw brand, product and growth marketing. With over 20 years of marketing experience, Wu has also held senior roles across Meta, Visa and American Express. At Meta/Facebook, she led the global consumer brand and product marketing for the Facebook App, most notably launching Facebook’s first brand campaign “More Together.” Her marketing teams have been awarded with numerous global advertising awards, including Bronze Lions at Cannes, and several shorty and clio awards for exceptional social content and campaign work. Wu has a BA in Economics and Asian studies from Tufts University, a MIA from Columbia University in International Affairs and Finance and also a Degree in Occupational Studies from Le Cordon Bleu Culinary Arts from the California Culinary Academy.
Topics:
Balancing data-driven growth with brand building
AI's impact on marketing strategy and team structure
Building inclusive teams and culture
#WomenInTech #CMOlife #TechLeadership #CareerGrowth

Jan 23, 2025 • 55min
Smart Venture Podcast watch party ft. StepStone Group Partner Seyonne Kang
EP160 StepStone Group Partner Seyonne Kang
Seyonne Kang is a Partner at StepStone Group. As of September 30, 2024, StepStone was responsible for approximately $682 billion of total capital, including $176 billion of assets under management. She is a member of the private equity team, focusing on venture capital and growth equity investments. Prior to StepStone, Ms. Kang was a partner with Greenspring Associates, a venture capital and growth equity investment firm that merged with StepStone in 2021. Before that, she spent seven years in investment management with a focus on private capital. Before moving into investment management, Ms. Kang spent about a decade on Wall Street in institutional equities where she served in a variety of functions, including software stock research and distribution of IPOs, follow-on offerings and convertible financings. Ms. Kang earned an AB with honors from the University of Michigan at Ann Arbor and an MBA from the University of California at Berkeley.
You can learn more about:
1. Evaluation framework for first-time fund managers
2. How emerging managers can build credibility with institutional LPs
3. Advice on building long-term LP relationships from scratch

Jan 23, 2025 • 55min
Insight MD Nikhil Sachdev on Building Global Software & Fintech Giants
Nikhil Sachdev joined Insight Partners in 2020 as a Managing Director.
In his role, he works with companies in the software and fintech ecosystems starting at Series A and well beyond. He invests through a global lens, partnering with founders close to his homebase in California and stretching across the US into Europe, India, SE Asia and Latin America. He began his career advising technology companies at Goldman Sachs, where he was an investment banker focused on cloud and mobile. His start in the investing world came at private equity firm Bain Capital, where we took an operational lens to investing and partnering with companies. He developed a passion for how businesses can play a positive role in helping better the world. This passion led him to Harvard Business School, where he had a chance to spend his summer working with the founder of a Sequoia-backed startup, which sparked his interest in technology and inspired him to pursue a career in venture capital.
After HBS, he joined Altimeter Capital, a long/short equity hedge fund that was scaling a venture capital practice. As a Partner at the firm, he led investments in multiple venture and growth stage private companies across the SaaS, DevOps, cloud infrastructure, Internet marketplace, gaming, and social media categories. At Insight, he has the privilege of working with founders and teams who imagine how technology can better the world and are actively building category-defining and enduring businesses. Silicon Valley is his home although he is traveling often.
Topics:
Key metrics to evaluate AI companies versus traditional SaaS
The moats and defensibility of different AI companies
Key patterns across successful AI companies

Jan 21, 2025 • 60min
Mo Islam: Threshold Partner Exploring Frontier Tech's Transformative Potential
Mo Islam is a Partner at Threshold Ventures. He focused on enterprise and frontier technologies. He sits on the boards of Benepass, EdgeQ, Elementary Robotics, Freeform, OpsLevel, Yellowbrick Data, and several stealth companies. He has also been involved with Threshold's investments in Atomwise, Imagen, Mythic, and Upside Foods. Mo was on the technology team at In-Q-Tel, where he conducted technical diligence on behalf of the CIA. Mo also held engineering roles at Lockheed Martin, the National Science Foundation, and the Pacific Northwest National Laboratory.
Mo is an author in a chapter addressing the disruption of employment by the rise of automation and artificial intelligence in Disrupting Unemployment: Reflection on a Sustainable, Middle-Class Economic Recovery. Mo graduated with a BS in electrical engineering, with interdisciplinary honors in international security studies, and an MBA from Stanford University. In 2018, Mo was named to Business Insider’s list of Silicon Valley biotech stars. He was also featured in the 2017 Forbes 30 under 30 Venture Capital list.
Topics:
Emerging trends in enterprise software and developer tools
AI's transformative potential across industries
Enterprise technology investment strategies

Jan 20, 2025 • 1h 8min
Geek Ventures' Ihar Mahaniok: Seed Investor Behind Tech Unicorns
Ihar Mahaniok, Founder and Managing Partner, is an immigrant engineering leader turned investor. Ihar grew up in Belarus, where he studied Computer Science. He has over 20 years of experience building code, ML models and engineering teams for startups and conglomerates, including Google & Meta. As an angel investor, Ihar invested in 150+ startups. Companies he has backed at seed include unicorns such as Instacart, PandaDoc, People.ai, Airbyte, and Jeeves.
Evaluates technical talent and engineering culture as an investor
Emerging ML/AI opportunities
Key lessons and challenges moving from engineering to investing


