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olivia@inspiredcapital.com

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Olivia Hazlehurst
Operations Assistant

about

Olivia is the Operations Associate at Inspired Capital, where she plays a key role in keeping the firm running smoothly — supporting day-to-day operations and ensuring both the internal team and portfolio companies have what they need to operate at their best.

Prior to Inspired, Olivia was in sales at Rippling, where she partnered with businesses to modernize their HR and IT operations through Rippling's suite of workforce management solutions.

Olivia holds a B.S. in Finance and Sales from the University of Alabama.

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olivia@inspiredcapital.com

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rose@inspiredcapital.com

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Rose Handaly
Executive Assistant

about

Rose is the Executive Assistant to Inspired Capital's Co-founder and Managing Partner, Alexa von Tobel. Prior to joining Inspired, Rose gained finance and operations experience at a family office and a publicly traded real estate investment trust.

Rose holds a B.S. in Business Administration from Northeastern University, concentrating in Finance, Entrepreneurship, and Corporate Innovation.

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rose@inspiredcapital.com

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willow@inspiredcapital.com

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Willow Pae
Platform Associate, Content & Communications

about

Willow is a Content and Communications Associate on the Platform team at Inspired Capital, bringing Inspired's platform, portfolio, and community to life through content and storytelling. She also produces the Inspired with Alexa von Tobel podcast, featuring conversations with world-renowned founders, including Ben Lamm of Colossal Bioscience and Mikey Shulman of Suno.

Prior to Inspired, Willow was a marketing specialist at FERMÀT Commerce, a Series B SaaS startup, where she focused on building brand presence and supporting growth initiatives. She began her career at NBCUniversal as part of the Page Program, rotating through marketing teams including Ad Sales, Peacock, and the Today Show, while also working with late night programming, including The Tonight Show Starring Jimmy Fallon and Saturday Night Live.

Willow holds a B.S. in Computer Science and Acting/Film from the University of Wisconsin–Madison.

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willow@inspiredcapital.com

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isabelle@inspiredcapital.com

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Isabelle Holt
Platform Associate, Network

about

Isabelle is the Platform Associate at Inspired Capital, where she supports portfolio companies by driving value-creation initiatives, building connections, and helping founders access the resources they need to scale.

Prior to Inspired, Isabelle worked in strategy consulting at Trinity Life Sciences, where she partnered with biopharmaceutical and biotechnology companies on commercialization strategy, opportunity assessments, forecasting across early clinical-stage and in-market assets, and portfolio planning. Her work focused on distilling large sets of primary and secondary market research into clear, actionable strategies.

Isabelle holds a B.S. in Global and Public Health Sciences and Business from Cornell University.

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isabelle@inspiredcapital.com

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gellman@inspiredcapital.com

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Alexa Gellman
Chief of Staff

about

Alexa is Chief of Staff at Inspired Capital, where she supports Founder and Managing Partner Alexa von Tobel on new and existing investments, fundraising, and firm strategy. She was initially drawn to venture capital for its unique blend of quantitative and qualitative skills, both essential for making successful investments and building strong partnerships with portfolio companies.

Prior to Inspired, Alexa was a Senior Associate at Volition Capital, a Boston-based growth equity firm, and an independent finance and operations consultant for early-stage companies. She began her career at BlackRock in New York City, spending five years across the BlackRock Alternatives business focused on fundraising, development of new investment capabilities, operating platform enhancements, business acquisitions and integrations, and sustainability initiatives.

Alexa holds a B.A., cum laude, in Economics from Harvard College and an M.B.A. with distinction from Harvard Business School.

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gellman@inspiredcapital.com

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chris.huether@inspiredcapital.com

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Chris Huether
Chief Financial Officer

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Chris is the CFO at Inspired Capital, where he manages all financial and internal operations of the firm. After nearly a decade in public markets, Chris found that venture capital channels his passion for building and solving complex problems.

Prior to Inspired, Chris was the CFO of Pruven Capital, an independent venture firm launched in partnership with Prudential. Before that, he worked on Prudential's IR and M&A teams, helping the company engage with investors and sell-side analysts and completing over $500 million in acquisitions globally. Chris is also a member of the Board of Directors of VCBC, the largest industry association of venture capital finance professionals.

Chris holds an M.B.A. from Columbia University and a B.S. in Finance and Accounting from Lehigh University.

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chris.huether@inspiredcapital.com

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annie@inspiredcapital.com

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Annie Shapiro
VP, Platform

about

Annie is the VP of Platform at Inspired Capital, where she partners across the portfolio to help founders access resources, introductions, and advice. She has spent 15 years in the New York tech ecosystem, operating at all stages throughout the startup lifecycle, with deep experience in marketing across both consumer and B2B, focused on brand messaging and communications. Since 2019, she has produced Inspired's weekly award-winning podcast, For Starters with Alexa von Tobel. In 2021, she joined the VC Platform Global Community as a Board Member and served as Vice President of the Board for 5 years.

Annie began her career as one of the first employees at LearnVest, where she spanned marketing, product, and business development — leading the company through milestones including LearnVest Live events nationwide, the launch of Financially Fearless, and the announcement of the Northwestern Mutual acquisition. Prior to Inspired, she was Director of Marketing at Namely, the HR tech startup.

Annie holds an A.B. in Art History and Italian from Princeton University.

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annie@inspiredcapital.com

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jonathan@inspiredcapital.com

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Jonathan Frankle
Venture Partner

about

Jonathan is a Venture Partner at Inspired Capital. He is the Chief Scientist (Neural Networks) at Databricks, which acquired his previous startup MosaicML — a company dedicated to making it easy and cost-effective for anyone to train large-scale, state-of-the-art neural networks. Jonathan also works on technology policy related to AI, including with the OECD to implement the AI Principles he developed in 2019, and previously served as the inaugural Staff Technologist at the Center on Privacy and Technology at Georgetown Law.

Jonathan completed his Ph.D. at MIT and holds a B.S.E. and M.S.E. from Princeton University.

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jonathan@inspiredcapital.com

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ming@inspiredcapital.com

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Ming Fang
Venture Partner

about

Ming is a Technology Venture Partner at Inspired Capital, bringing over 25 years of engineering experience with an emphasis on finance and advertising applications. Most recently, Ming was the Technology Fellow and Chief Architect at LearnVest. Prior to LearnVest, he was VP of Engineering and Architecture at PulsePoint, Architect at RBC Capital Markets, and Enterprise Architect at OTC Markets Group. His experience also spans large financial institutions including JP Morgan and Merrill Lynch.

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ming@inspiredcapital.com

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luke@inspiredcapital.com

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Luke Bender
Investor

about

Luke is an Investor at Inspired Capital. Prior to joining Inspired, Luke patented AI infrastructure and built applied AI agents at Microsoft. He was also a Forward Deployed Engineer and Builder at multiple early-stage AI companies, including Regal, and has led content strategy for an emerging VC while advising and investing in various AI startups.

Luke holds a B.A. in Computer Science and Philosophy from Duke University.

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luke@inspiredcapital.com

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chris@inspiredcapital.com

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Chris Brown
Partner

about

Chris is a Partner at Inspired Capital and a career institutional venture investor who has spent the past decade working with early-stage teams. He balances a deep understanding of later-stage and public markets with an appreciation for early-stage product building, often serving as a company's first check and helping teams bridge the gap between the zero-to-one phase and the realities of hyperscale. He strongly believes that innovation will look different over the next decade as complex sectors like financial services, healthcare, logistics, and energy — the areas of our economy least touched by past technological platform shifts — demand new products.

Prior to Inspired, Chris was an investor at First Round Capital. He began his career at The Blackstone Group.

Chris holds a B.A. in Political Science and Economics from Middlebury College.

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chris@inspiredcapital.com

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kamran@inspiredcapital.com

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Kamran Ali
Partner

about

Kamran is a Partner at Inspired Capital. He brings over a decade of experience supporting companies at every stage of growth — from pre-revenue through IPO. He takes pride in often being a founder's first institutional investor and believer, and is dedicated to building high-conviction, high-trust relationships with the entrepreneurs he partners with.

Prior to Inspired, Kamran was an investor at Point72, where he worked across public and private markets on venture, growth, and private equity investments, including the acquisition of the New York Mets. He began his career in investment banking at Goldman Sachs, first in the Consumer, Retail, and Healthcare Group and later in the Financial Institutions Group, working on M&A, IPOs, spin-offs, and activism defense.

Kamran has been recognized as a Forbes 30 Under 30 in Venture Capital and holds a B.A. in Economics and Public Policy from Dartmouth College.

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kamran@inspiredcapital.com

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charlotte@inspiredcapital.com

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Charlotte Ross
Partner

about

Charlotte is a Partner at Inspired Capital, having been with the firm since its inception in 2019. She has had the opportunity to see dozens of businesses scale, gaining insight into what drives growth and resilience, and has built strong, trust-based relationships with founders as a steady partner through the ups and downs of a startup's journey.

Prior to Inspired, Charlotte was an investor at New Enterprise Associates (NEA), where she led investments in and sat on the boards of Duolingo, Framebridge, Mejuri, The Wing, and others. She began her career as an Investment Banking analyst in the Technology, Media, and Telecom group at Goldman Sachs, working on M&A and capital markets transactions for software and consumer internet companies.

Charlotte has been recognized as a Forbes 30 Under 30 in Venture Capital and holds a B.A. in Economics from Yale University.

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charlotte@inspiredcapital.com

Lucy Deland

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lucy@inspiredcapital.com

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Lucy Deland
General Partner
Lucy Deland

about

Lucy is a General Partner at Inspired Capital. Prior to Inspired, she was on the founding team at Paperless Post, where she spent a decade as COO building the company to serve over 100 million hosts and guests. Over the course of a decade, she led key areas of the business including finance, product management, data analytics and infrastructure, consumer insights, and strategy — instrumental in transforming Paperless Post from a concept in a living room to a global platform with 100 million users.

Lucy began her career at Insight Venture Partners before joining Alexa and James Hirschfeld to start Paperless Post in 2008.

Lucy holds an A.B. in Psychology from Harvard College.

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lucy@inspiredcapital.com

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mark@inspiredcapital.com

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Mark Batsiyan
General Partner

about

Mark is a General Partner at Inspired Capital. As an investor, Mark is deeply committed to guiding founders through the evolution of business models and strategy as their companies scale. In addition to his investing role, Mark served as the firm's COO through 2023, managing all fund operations.

Prior to Inspired, Mark was a Partner at Northwestern Mutual Future Ventures, which he helped launch and scale in 2016. He joined Northwestern Mutual following the acquisition of LearnVest, where he was a member of the senior leadership team overseeing strategy and business development. At LearnVest, he launched the enterprise business, LearnVest at Work, and signed several key partnerships ahead of the company's 2015 acquisition. Mark began his career as a consultant at Oliver Wyman and spent time as a public markets investor at Solas Capital Management. Notable investments from his time at Northwestern Mutual Future Ventures include Chime, OJO Labs, Ladder, Gabi (acquired by Experian), and LiveOak Technologies (acquired by DocuSign).

Mark holds an A.B. in Philosophy from Princeton University and an M.B.A. from Columbia Business School.

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mark@inspiredcapital.com

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penny@inspiredcapital.com

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Penny Pritzker
Co-Founder

about

Penny is a Co-Founder of Inspired Capital. A repeat founder and former U.S. Secretary of Commerce in the Obama Administration, Penny has more than 30 years of experience across numerous industries and has dedicated her career to uplifting visionary founders tackling urgent global challenges. Her partnership with Alexa began when Alexa was named a Presidential Ambassador for Global Entrepreneurship — co-founding Inspired Capital was a natural next step, uniting their shared commitment to fostering entrepreneurship in America and around the world.

In addition to Inspired Capital, Penny is the founder and Chairman of PSP Partners and its affiliates, including Pritzker Realty Group, PSP Capital, and PSP Growth. Over the course of her career, she has founded Vi Senior Living and co-founded The Parking Spot and Artemis Real Estate Partners. She is a member of the boards of Microsoft Corporation, DEPT, and Icertis, and in July 2022 was elected Senior Fellow (chair) of the Harvard Corporation — the first woman to hold the position. Penny previously served as President Biden's Special Representative for Ukraine's Economic Recovery and has held board roles at the Carnegie Endowment for International Peace, the Council on Foreign Relations, and Stanford University, among others. She has also served on President Biden's Council of Advisors on Science and Technology, and President Obama's Council on Jobs and Competitiveness and his Economic Recovery Advisory Board.

Penny holds a B.A. in Economics from Harvard University and a J.D. and M.B.A. from Stanford University.

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penny@inspiredcapital.com

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alexa@inspiredcapital.com

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Alexa von Tobel
Founder & Managing Partner

about

Alexa founded Inspired Capital because she deeply understood the unique challenges of the founder journey. Before Inspired, she dropped out of Harvard Business School to launch LearnVest, one of the first fintech companies aimed at making financial planning software accessible to millions. Discouraged by the capital partners available in NYC at the time, Alexa promised herself she would one day become the kind of investor she wished had existed. In 2015, LearnVest was acquired for nearly $400 million, marking one of the decade's largest fintech acquisitions.

Following the acquisition, Alexa became Northwestern Mutual's first-ever Chief Digital Officer, leading product and technology strategy as the company achieved $30 billion in annual revenue, before becoming Chief Innovation Officer overseeing their venture arm. Her career began on Morgan Stanley's Proprietary Trading Desk, before she helped build Drop.io, an early-stage startup later acquired by Facebook.

A 2016 Henry Crown Fellow and inaugural member of President Obama's Ambassadors for Global Entrepreneurship, Alexa has been recognized with a Forbes cover, Fortune's 40 Under 40, Most Powerful Women, Inc. Magazine's 30 Under 30, and World Economic Forum Young Global Leader. She is the New York Times bestselling author of Financially Fearless, Financially Forward, and Money Matters. Alexa holds an A.B. in Psychology with Honors from Harvard College.

Contact

alexa@inspiredcapital.com

Max Shaw and Brian Distelburger on Reinventing People Management with Windmill

Alexa von Tobel

Windmill co-founders Max Shaw and Brian Distelburger are building the AI-powered people platform for how companies develop and manage their talent. Founded alongside Mark Tanner, Windmill replaces the broken, once-a-year performance review with something faster, smarter, and that employees actually love. Since launching in November 2025, they've reached more than 100 customers including Kalshi, The Farmer's Dog, and Rho, and Inspired is so proud to have led their recent seed round. As AI makes every employee more powerful, the companies that win will be the ones that put the best talent in exactly the right role.

What You'll Learn:‍

• Why the current state of performance management is broken
• How AI will change the relationship between managers and their teams
• What the future of work looks like as companies grow more complex
• Why skills assessment is about to become one of the most important things a company can do
• Why Max and Brian are optimistic that AI will benefit people at work

Chapters:

00:00 Introduction 
02:33 Meet Max and Brian 
03:44 What Is Windmill 
05:38 The State of Performance Reviews 
09:20 Where Windmill Is Headed 
13:20 AI Coaching for Every Employee 
16:15 Why They Chose This Problem 
18:33 The Biggest Change Management Moment of Our Lives 
24:15 Early Traction and What's Working 
27:30 Where the World of Work Is Going 
34:55 The IKEA Example 
36:16 Skills Assessment and Workforce Redeployment 
41:18 Why New York 
43:35 Quickfire

‍Follow Max, Brian, and Windmill:
• Website
• LinkedIn
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• Max's LinkedIn
•Brian's LinkedIn

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• LinkedIn
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• Instagram

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