E648: All #AskJason: cannabis, education, diversity, real estate, funding & more at #TWiSTlive, Microsoft Reactor



about this episode

In episode 648 of This Week in Startups, Jason opens up his office hours to an audience of investors and entrepreneurs at the Microsoft Reactor in San Francisco to answer questions and analyze pitches. One by one, founders take the stage to pitch their products or simply to pick Jason’s brain. J.P. Martin of GrowX, Katherine Webster of Vets in Tech, and Keenan Williams of REZI, are just a few of the hard working entrepreneurs who stand up to hear Jason’s candid feedback on their ideas.


0:37-7:22: Jason introduces himself by explaining his passion for entrepreneurship and startup investment.

7:22-9:10: J.P. Martin of GrowX pitches his cannabis based business to Jason.

9:10-10:21: Jason responds to the pitch by explaining that J.P. is entering the market at the right time, maybe even slightly early due to the fact that cannabis will be legal, on a federal level, within our lifetime.

11:52-20:05: “The question I have for you about this business is: What’s defensible about it?”

22:15-23:13: Katherine Webster of Vets in Tech asks a question on behalf of veteran entrepreneurs, but applies to all entrepreneurs.

23:13-28:14: Jason gives his top advice for entrepreneurs raising money: “Doing your research on investors (is critical).”

28:14-30:44: Jason shares the real purpose of a first meeting… to get a second meeting.

30:44-33:07: Keenan Williams of REZI pitches his product, which he describes as “an apartment rental experience for the future.”

33:07-36:34: Jason has some serious concerns about the competition in Keenan’s space.

36:34-39:32: “Red pill or blue pill? Do you want to stay in the Matrix, or do you want the best advice?”

39:32-42:21: Jason gets passionate about focus.

42:21-44:18: Carla Mays of Mays Civic Innovation explains her product and the obstacles she is facing in the civic tech space.

44:18-53:00: The reality is that investors automatically look at civic organizations differently because truthfully, investors only want “marauding capitalists,” not charities.

53:00-54:08: Brian Bensch asks about Jason’s thoughts on “Ramen Profitability” for early stage founders.

54:08-56:30: Jason believes that while the “Ramen Profitability” strategy is good advice, it really only applies to the young entrepreneurs who have no kids and are straight out of school.

56:30-59:00: Brian’s second question involves the dilemma of “pivot vs. persevere.”

59:00-1:04:14: Cynthia Harrington of Team You pitches her educational performance platform.

1:04:14-1:12:06: After pitching, Cynthia follows up with a question on how to think about valuation as she approaches her series A round.

1:12:06-1:16:38: Lastly, Abel Villca Roque of Villca Solutions asks about the next phase for a company with a finished product and revenue.

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