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Invest Like a Boss

168: Drew Bledsoe, from Pro Football to Wine Estates

Invest Like a Boss

Sam Marks Johnny FD Derek Spartz

Business, Investing

4.8 β€’ 518 Ratings

πŸ—“οΈ 26 January 2021

⏱️ 65 minutes

🧾️ Download transcript

Summary

Upon his retirement from the NFL in 2007, Drew Bledsoe "doubled back" to his hometown of Walla Walla, Washington to realize a long held dream. Drew and his Wife, Maura, purchased a piece of property on the southern edge of the Walla Walla Valley AVA and subsequently launched Doubleback as an estate focused winery with the goal of crafting America's best Cabernet Sauvignon in an elegant, true to varietal way. Drew had long been planning for this moment during his years playing football and success came immediately as the very first vintage earned a spot in Wine Spectator's Top 100 List.

Drew hired Josh McDaniels, now CEO & Director of Winemaking, away from Figgins Family Wine Estates where he had trained for almost a decade under their longtime mentor and friend, Chris Figgins. Josh, also a Walla Walla native, has been named a "Washington Prodigy" and a "Game Changer of Washington Wine" by Wine Enthusiast Magazine. The collaboration between Drew and Josh is a competitive partnership that pushes them to continue the pursuit of perfection in Cabernet Sauvignon every day.

Doubleback remains a small, family owned winery located on the southern edge of Walla Walla in its new home that was completed in 2018. The winery has four estate vineyards all located in the Walla Walla Valley and all unique to the other. Each vineyard is sustainably certified and farmed by its own incredible farming crew that is an integral part of the team. The team welcomes it's mailing list customers by appointment only daily.Β 

Listen to ILAB 168 on iTunes here or subscribe on your favorite podcast app.

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Where we are:

Sponsor:

Discussed:

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Time Stamps:

  • 10:42 – When did you know you wanted to go into the wine business?
  • 13:20 – Has Walla Walla always been producing really good wines?
  • 16:30 – What kind of investment advice is given to young athletes?
  • 21:20Β  – Have you had other crazy investment proposals during your career?
  • 24:58 – How was the transitioning for the NFL to the Wine Estates?
  • 29:05 – How did you start with Doubleback once you retired?
  • 31:06 – Did you know the economics of the wine business?
  • 34:15 – Why do you think a lot of winery businesses fail?
  • 40:06 – What are the future plans for the estates?
  • 44:08 – Do you see this business staying in the family?Β 
  • 50:26 – Sam and Derek review

If you enjoyed this episode, do us a favor and share it! Also if you haven’t already, please take a minute to leave us a 5-star review on iTunes and claim your bonus here!Β 

Copyright 2021. All rights reserved. Read our disclaimer here.

Transcript

Click on a timestamp to play from that location

0:00.0

Hey bosses, before we kick off this episode, let me tell you about our sponsor, Our Crowd.

0:05.6

They got in on some of the best performing IPOs of 2019 and 2020, and now they want to get you in on what's next.

0:13.1

Our Crowd offers accredited investors access to invest directly, easily, and most importantly, early.

0:20.1

They just put a new listing on their site for a company called Nanoloc Security.

0:25.4

I'm going to tell you all about that company during the break, but if you want to check it out now,

0:29.6

just go to our crowd.com slash boss.

0:33.0

That's O-U-R-C-O-W-D dot com slash B-O-S-S. All right, let's kick off this episode of an

0:41.8

Invest like a Boss. Welcome to the Invest like a Boss podcast. I'm Sam Marks and I'm Johnny F-D.

0:47.6

We're self-made entrepreneurs who invest our own money and use modern technology to invest like a

0:51.5

boss. Join us each week for exclusive interviews with our network of modern investors,

0:55.5

business owners, and multimillionaires to discover new ways to invest our hard-earned cash.

1:02.4

Welcome back, everybody, to episode 168 of Invest Like a Boss.

1:07.5

This is Sam Marks.

1:08.4

I'm staring out the window right now at the Bangkok skyline. I'm just nestled

1:13.9

in for four days, actually 14 days. I'm on day four of a 14 day quarantine. So it's great to be back

1:20.9

with Derek for a little bit of company. I've been waiting to hear from you, buddy.

1:26.6

I can tell. Usually it takes Sam Marks a little bit of time to get back to hear from you, buddy. I can tell.

1:28.2

Usually it takes Sam Marks a little bit of time to get back to you when you have a question,

1:32.2

but he is all over it right now.

1:34.3

I can tell you're bored, Sam.

1:36.8

This is how I used to operate pre-business exit.

1:40.8

Then I got a bit laxidazil, but I'm back on it now because I'm literally in

...

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