How I Invest with David Weisburd

E409: The Leadership Lessons That Built a $6.5 Billion Firm


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Most investors chase what's exciting. Jason Koenig built a $6.5 billion firm by investing where almost nobody was looking.
In this conversation, Jason explains why overlooked industrial assets can produce exceptional long-term returns, how ITE grew from $60 million to $6.5 billion in assets under management, why culture compounds just like capital, and the leadership lessons he learned while scaling an investment firm from startup to institutional platform.
Highlights:
  • Why the best investments are often hiding in overlooked industries.
  • How Jason spotted a billion-dollar opportunity by watching trains.
  • The founder mindset required to build conviction before everyone else.
  • Why culture becomes a firm's biggest competitive advantage as it scales.
  • The leadership framework behind hiring years before you actually need people.
  • Why compensation should reward teamwork, not individual empires.
  • The psychology every great investor must understand.
  • Lessons from negotiating against Carl Icahn.
  • Why entrepreneurs need both conviction and humility.
  • The career advice Jason wishes he had followed much earlier.
  • Guest Bio:

    Jason Koenig is the Founder, Managing Partner at ITE Management, an investment firm specializing in transportation infrastructure and industrial real assets. Since founding the firm in 2013, he has grown ITE from a startup into a platform managing $6.5 billion in assets, with approximately $13.5 billion of assets owned and managed. Before launching ITE, Jason held investing and legal roles at Avenue Capital, Hale Capital Management, Kirkland & Ellis, Latham & Watkins, and Cooley. He earned an MBA from the Wharton School and graduate degrees from the University of Michigan.

    Are you interested in sponsoring the How I Invest Podcast? Please email David Weisburd at [email protected].

    We’d like to thank AlphaSense for sponsoring this episode!

    Sponsor:

    AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

    Stay Connected with David Weisburd:

    X/Twitter: @dweisburd

    LinkedIn: https://www.linkedin.com/in/dweisburd/
    Weisburd Pierce: https://www.weisburdcapital.com/

    Stay Connected with Jason Koenig:

    LinkedIn:https://www.linkedin.com/in/jason-koenig-goblue/

    Questions or topics you want us to discuss on How I Invest? Email us at [email protected].

    Disclaimer:

    This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Pierce. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

    (0:00) Why Everyone Ignored a $6.5B Opportunity
    (2:46) From $60M to $6.5 Billion AUM
    (8:34) The Entrepreneur's V-Shaped Ego
    (15:17) Why Great Leaders Need Humility
    (25:13) The Hardest Part of Scaling a Firm
    (31:09) Hire 3 Years Before You Need Them
    (35:02) The Best Career Pattern for Leaders
    (43:37) How Great Cultures Police Themselves
    (46:19) Why Investing Is Really Psychology
    (57:02) The Career Advice Everyone Gets Wrong
    ...more
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