Angel Invest Boston

Through the Angel Invest Boston Podcast we seek to learn more about the creation of world-changing startups. Boston’s unique concentration of academic talent and entrepreneurial culture offer bountiful opportunities for conversations with people who have funded and built innovative companies. By recounting engaging stories, angels and founders convey lessons they have learned. These narratives illustrate the rewards of helping founders commercialize transformative technologies. We hope you too will find our dialogues entertaining and instructive. I’m Sal Daher, host of the Angel Invest Boston Podcast. After immigrating to Boston as a child and attending Belmont High School, I studied engineering at MIT and Stanford. Decades of work in international finance followed. During that time, I invested in a handful of ventures founded by friends and acquaintances. Now, I’m a member of Walnut Ventures and MIT Angels and spend most of my time as an angel investor taking stakes in about a dozen startups per year.
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Angel Invest Boston




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Now displaying: August, 2018
Aug 29, 2018

His bonhomie masks a keen intelligence that has, for decades, taken note of what makes or breaks founding teams. Joe Caruso is the CEO Whisperer, the Father Confessor to Founders. Joe’s an intrepid angel investor who goes where other angels fear to tread. This makes him a highly sought-after board member or advisor. I was privileged to sit down with him for an hour and to imbibe his wisdom and good humor. Typical Joe Caruso comment: “…you don't train a Labrador to flap its ears. It makes for a lousy butterfly.”


Here are some highlights of what we discussed:

  • Joe Caruso Introduction
  • Joe Caruso Bio
  • How Joe Discovered He Wanted to Be the Father Confessor to CEOs
  • How Roxbury Latin School, the One True School, Figured in Joe Caruso’s Formation
  • Joe Caruso Drops Out of High School and Enrolls at Northeastern University
  • Boston’s Unique Environment for Learning: Jeff Bezos Take Note
  • “I'm in the cafeteria … and at the table is a newspaper from the prior June … and they had a list of starting salaries of all the people who graduated, and electrical engineers made more than anyone else, so I said I guess I'll be one of them.”
  • “…co-op [work/study program at Northeastern] taught me that engineering wasn't my strong suit.”
  • Outstanding Argument in Favor of Northeastern’s Co-op Program
  • Delightful Story About Joe Caruso Considering Turning Down Harvard Business School
  • Joe Caruso Had No Idea of the Value of Networking While at Harvard Business School!
  • “I studied and ... I took no advantage of that [networking at HBS], which in retrospect was a huge missed opportunity.”
  • How Doing Turnarounds Got Joe Caruso Involved with Level Up
  • “Here's this 19-year-old kid, either freshman or sophomore at Princeton, that was going to drop out to start a company.”
  • “It had gaming, location-based. As I kidded with him, it was very buzzword-compliant.”
  • “If you give me a bright, passionate, high-integrity entrepreneur, that's the ticket of admission to at least me considering investing.”
  • Semyon Dukach’s Answer to “Should I Start a Company?”
  • “…you don't train a Labrador to flap its ears. It makes for a lousy butterfly.”
  • “None of this is off-topic. … Our topic is human nature.”
  • “So, be who you are. That also says, "complement who you are."”
  • The Change in Business Plan of Which Joe Caruso is Proudest
  • From Measuring Alpha Waves to Helping People Recover from Spinal Injuries
  • Leveraging Personal Computers for Lab Automation
  • The Particular Hell of VCs with Conflicting Interests
  • Sal Daher Reads the Review from Listener bpaul2 – Reminds You to Leave a Review in iTunes
  • Joe Caruso’s Favorite Pivot
  • Joe Caruso’s First Investment
  • Joe Caruso’s Parents Were Survivors of the Depression Era and thus Not Open to Entrepreneurship
  • "We've gotta get you out of the basement."
  • Joe Caruso’s Apologia for the Value of Boards – Directors vs. Advisors
  • What Advice Do You Find Yourself Giving Over and Over?
  • Joe Caruso’s Parting Thoughts
Aug 15, 2018

Few are as well positioned to see the huge opportunities that exist for small and medium businesses in digital marketing as the founder of Constant Contact. In his new company, Brevi, Randy Parker is using software to allow mom & pop businesses to access those opportunities in ways that pay.

I had loads of fun talking to this most clever and affable guest; and I learned a lot.

Here’s what we touched on:

  • Randy Parker Introduction
  • How Randy Parker Discovered He Wanted to Build Software
  • What Took Randy Parker from Florida to MIT
  • “So, I was third generation entrepreneur. My kids now I say are fourth generation entrepreneurs when they're doing things.”
  • “…in a consultant practice it's always, essentially, you're usually being hired to solve something that other people haven't figured it out.”
  • “I grew up in a family thinking about A/B tests, and marketing…”
  • Roving Software / Constant Contact Started as an Information Agent for Business
  • Constant Contact Was Essentially a SaaS Business by Another Name
  • Sal Daher Thanks Listener JaySingh1022 for an iTunes Review – Asks for Your Review
  • What Brevi, Randy Parker’s Current Startup, Does
  • “The way we can do that [allow the local coffee shop to compete with Starbucks] is, to actually tap into their data.”
  • Brevi Ties into the Small Business’ Operating Software to Learn About Opportunities for Growth
  • “…there is no substitute for the integrity and the commitment to the small business.”
  • Intuit’s Scott Cook as the Model of Attention to All Customers
  • For 2019, Randy Parker Hopes to Give Users a Tangible ROI on Their Ad Spend
  • Thriving on the Abundance of Data, Machine Learning Can See Patterns Humans Can’t
  • Randy Parker and the Proto-Kindle
  • Alice’s Table
  • Outseta
  • “…startups are like a family. And so, like families, there are some great things about them and there may be more challenging things about them.”
Aug 1, 2018

Invest Alongside Boston's Top Angel in Our Syndicates: Link to Syndicates Page

Angel investors Catherine Friend White and Ben Littauer answered questions about investing in startups in front of an audience at Babson College. Then the audience got to ask questions. The conversation ranged from the optimal portfolio size to the usefulness of the blockchain.

Here are some highlights:

  • Sal Introduces Live Event - Thanks Nina Block & Margaret Jone from Babson for Making it Possible
  • Sal Introduces Angel Catherine Friend White
  • Sal Introduces Angel Ben Littauer
  • How Catherine Became an Angel Investor
  • How Ben Became an Angel Investor
  • “…there are about 32 [angel groups] here in New England…”
  • “…I have so many soft values that I get from doing this [angel investing]…”
  • KnipBio & UltraCell
  • Cognition Therapeutics – Susan Catalano
  • “Having run my own company for 27 years, I have also my own list of what not to do…”
  • “If you have 25 [investments], you can probably diversify away a fair amount of the risk.”
  • “One of the biggest mistakes that early investors make is, they have a good outcome on their first bet and then they think they can pick winners.”
  • “…angel deals are chronically underfunded in the Boston area…”
  • “…when you're providing growth capital you need to keep providing more.”
  • NextShift Robotics
  • ICOs
  • “…I think that there is a lot of value in blockchain, but there's a lot of swamp around the blockchain ecosystem…”
  • “The other thing to know about blockchain is that the NSA has cracked it.”
  • Potential of Using the Blockchain for Storing Medical Records
  • Maybe This Is a Situation Where an ICO Makes Sense
  • Coachability Is Crucial for Founders
  • "I am going to be the forever CEO."
  • “…come to us and ask for advice, you might get money.”
  • Golden Seed Office Hours & The Capital Network, TCN, as Great Resources
  • Q&A: Joel Francois of Helius Power
  • Q&A: Ankit Soni of Cricket++
  • Q&A: Bob Goodof of Walnut Ventures
  • Q&A: Brett Wagner of Waec LLC