July 07, 2021

Growing Your Business and Facing Adversity with Drew Bledsoe, Quarterback and Entrepraneur

Dana Safa

1Huddle Podcast Episode #2

On this Bring It In podcast episode, 1Huddle’s CEO and Founder Sam Caucci sat down with Drew Bledsoe, former NFL Quarterback, and business owner. After being a professional football player for 11 years, he opened up his own winery, Doubleback.

On this episode of Bring It In season one, Drew sat down with Sam and discussed facing adversity, growing your business, and marketing.

Audio available on Apple Podcasts, Spotify, and Google Podcasts. 


Below are some of the insights Drew shared during our chat, edited for length and clarity. You can find more Bring It In podcast episodes here.

  • “When times are crappy, that’s when a good team separates from an average team.”
  • “It’s a chance to really start being efficient, the chance to take a hard look at everything you’re doing and analyze every piece of your business and figure out where you can get better, because you have to.”
  • “And now, rather than just growing like you were growing before, when times turn around and things get back to some semblance of normal, now you’re a much better company and really are set up to sail.”


Sam: Is there a challenge that you can draw upon, whether it’s in your career or in your current business that you faced, is there a certain challenge you’ve come across that you think you call upon or think back to in kind of moments like this that we’re in today?

Drew: Well at a high level, one of the things that we’ve done at our company is we’ve learned to embrace adversity almost to the point where we look forward to it. And that comes out of football and into business. You know when you’re playing ball, it’s often hard to continuously improve when times are good. You know, when you won your last three games, you’re feeling pretty good and you’re like, okay, we’ll just keep doing what we’ve been doing and that’s been successful. But when you get hit in the face, you’re like, okay, well. You lose a couple of games in a row, man, we’ve got to take a hard look at what we’re doing. 

And in our business, we’ve been clicking along pretty good and it’s been a successful run. But the times that we’ve had adversities in our business, whether that’s a weather issue, whether it’s a personnel issue, whether it’s a market issue, whether it’s a distribution problem, every time we’ve faced one of those adversities, we’ve come out the other side as a much better.

And that’s been very much the case right now. We’ve had to adapt to that changing sales environment where we’re doing more virtual tastings. We’re doing zoom meetings online. We’re reaching out and talking to customers directly rather than just sending emails and doing social media. We’re actually getting on the phone and talking to people.

And all of those initiatives have been extremely effective for us to the point where our sales are actually up rather than down going through this economic debacle, we’re in the middle of.

Sam: What do you think it’s going to change about business? You mentioned earlier when we were talking that some stuff is going to change for the better possibility, but what do you see that’s going to be changing coming out of this for a moment, the way you operate your business? 

Drew: Well, you know, it’s forcing us to take a hard look at everything. Big picture, just pure business standpoint. We’re trimming fat, looking for waste, looking for things that we don’t need to be spending. And that’s the high-level piece of it. But more directly, we’re really trying to leverage technology,  zoom meetings, online promotions, more regular direct contact with our existing customers, as well as reaching out to the new customers. 

For our business, our very best marketing is customer recommendations to their friends. That’s the stickiest way we can market. And by having more high touch with our current customers, it’s encouraging them to share wine with their friends and share experiences with their friends, and giving them a story to tell when they open a bottle. So we’re really trying to leverage technology, which we were already doing, but this has forced us to accelerate that and really make that the focus of our business as we’re going through this because we can’t get face-to-face with people.

And so this has really forced us to take a hard look at some of those things. And some of them have been effective enough that we may eliminate some of the travel and some of the events that we’ve done in the past. They’re expensive. If I travel to New York City for a week, you got flights, you got hotels, you’ve got dinners, you got all of that, that are expensive things. And those will still be necessary at some level. But, some of them will be replaced with online virtual things, which cost us almost nothing relative to what we were paying to do events and do all the travel.

Sam: How big is your current team?

Drew: Our current team has grown a lot in the last few years. Two years ago, we had six employees total. We now have 28. We did a couple of things. We opened a new wine bar in Bend, Oregon, which is our full-time home, the wineries in Walla Walla. And then we also started our own farming company. So now we have total control from the dirt all the way to the glass. And so that’s where the biggest growth has been in just opening a new wine bar and starting the farming company.

We’re actually sort of a real business now. We left the startup phase after 13 years and are becoming a real business with 28 employees. And we’ve been able to keep everybody on with the exception of one who chose to leave. So at 28 people that becomes a different kind of animal than it was when there were just six of us.

Sam: It goes without saying you played for a lot of great coaches over the years when you were a player. Now is someone who’s leading an organization, have you learned anything different in the last few weeks when it comes to being a leader that you didn’t maybe think about before? 

Drew: Well, one thing that I felt like was a strength when I was playing quarterback, I felt like, and I think it was also something I would point to as a failure of mine as a quarterback, I felt like I was much better with my back against the wall than I was when things were going good. Matter of fact, if I look back at my career and I’m being totally honest, when we’re winning and rolling, my mind would wander a little bit and start thinking about other things even on the sidelines during a game.

But when I had my back against the wall, that’s when I felt like that was my focus was best and felt like I performed the best, and with our team, that’s been the leadership I’ve supplied was like, all right guys, look, this is where we separate. When times are crappy, that’s when a good team separates from an average team.

And so that guidance has been a challenge to our team. Like, Hey, this is not time to sit back and moan. The hard times that have been thrust upon us, this is a great opportunity to separate, and our team has really done that. We’ve got a high-functioning team and you really find out what you have from a team standpoint when times are bad. When times are good everybody just kind of rises with the tide, there was a Warren Buffet quote that went, ‘when the tide goes out, you find out who’s not wearing shorts.’

And for our team, as the tide has gone out, our team has stepped up and really performed at a higher level and they were performing just when things were clicking along, which has been cool to watch.

Sam: Great quote. 

Drew: That was a great quote, right? 

Sam: Last question for you. Any advice that you would give, any message like if you were in the huddle right now with CEOs across the country who are again, waking up, trying to figure it out, they’re not sure if they’re going to get a PPP check, they’re not sure when they’re going to actually get back to work, any advice from Drew Bledsoe? 

Drew: You know, there’s a list out there that you can Google of companies that were started in a depression or a recession. And most of the biggest companies in the world, and it was companies like GE, Apple, these massive, massive companies, almost all of them were started when times were hard.

So to the CEOs and to the people that are running businesses out there right now, when you go through times like this, it’s a chance to separate. It’s a chance to really start being efficient, the chance to take a hard look at everything you’re doing and analyze every piece of your business and figure out where you can get better because you have to. If you just sit back and go status quo when times are rough like this, you just get taken down.

But if you embrace times like this as an opportunity to really improve your business, then when times come back, you keep those same policies, those same procedures, those same initiatives in place when times are good. And now, rather than just growing like you were growing before when times turn around and things get back to some semblance of normal, now you’re a much better company and really are set up to sail. To the CEOs and people running businesses out there, I would look at this as a huge opportunity to really tighten up your business, really take a hard look at everything you’re doing so that when times come back around, man, you’re ready to fly.

Sam: Because you probably do that with like a few cases from your winery. I think that’ll probably help CEOs get through all the chaos.

Drew: I really think that drinking copious amounts of Doubleback during this downturn is almost a necessity for anybody that wants to grow their business. So if you want to find us, it’s Doubleback.com, order up some wine and it’s just gonna help you in every way.

Sam: That’s great. Yeah, I’m sold on that one. Appreciate ya. Appreciate you being here, drew.

Drew: Thank you so much, man.

Topics Discussed: Business, Leadership, Management, Adversity

Dana Safa, Manager of Digital Marketing at 1Huddle

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