When you think of enduring success in sports, few names fit the bill like world champion quarterback Joe Montana.

Over his 16-season career with the San Francisco 49ers and Kansas City Chiefs, Montana brought home four Super Bowl rings, three Super Bowl MVP wins, and a laundry list of records and achievements. Joe’s success even inspired a video game. Dubbed “Joe Cool” for his even-tempered approach to leadership, Montana remains one of football’s most beloved and recognizable figures.

After retiring from the Chiefs in 1995, Joe continued his track record of success in business, putting his experience into practice as an angel investor, venture capitalist, and mentor for founders building high-growth companies (including Vendr). 

In 2016, Joe and partners Mike Miller, Michael Ma, and Nathaniel Montana raised the first fund for Liquid2 Ventures, a micro-fund focused on seed-stage investment. The VC firm is now raising its third fund and has enjoyed several early wins including a successful exit of the DevOps platform GitLab.

Our team had the once-in-a-lifetime chance to sit down with Joe for our latest Vendr Visit. Over one exciting hour, Joe gave us an all-access pass to his career highlights, the best lessons he learned as a quarterback on the field to becoming a quarterback in startup investing, and the qualities that make a great leader.Joe Montana startup investor and former pro football player

Source: Forbes

Many roads to opportunity

Though the name Joe Montana is synonymous with football, Joe actually spent his school years competing as a three-sport athlete — baseball, basketball, and (of course) football. 

He considered entering college on a basketball scholarship until his top pick, Notre Dame, came knocking with a football one. Joe seized the opportunity to play for the Fighting Irish. 

“It was a tough decision, but it was my dream to go to Notre Dame.” The decision would ultimately set the trajectory of his professional life.

For Joe, the transition from a small-town high school to an elite college proved difficult. “I was so overwhelmed when I got there, both academically and athletically. It was the biggest football team I’d ever seen in my life — we had probably seven first-round picks.” This competitive field, complete with seven freshman quarterbacks, made for a difficult first year. 

After a tough start, Joe found his footing on and off the field. He put in the work academically and athletically, rising from seventh string to starter through his college football career. Though sidelined by a shoulder injury in his sophomore year, Joe returned to the field as a full-time starter for his junior year, leading the Irish to several celebrated victories.

This commitment to doing the work would open the door to his record-breaking NFL career, and later inform his work and vetting process as an investor.

Lessons from the field

1. Don’t rely on talent over-preparation 

If you ask Joe about his success in those early years, he’ll point not to talent but preparation as the cause.

 “By no stretch or means,” did he consider himself the most talented person on the team. As he explains, raw talent is only one aspect of success on or off the field. 

He thought one Notre Dame starting quarterback “was probably the most talented physically. [He was] gifted… he could run, jump, throw.” But as Joe explains, the young player had “a tendency to throw the ball to the guys with the other jerseys on.” While his talent secured him a spot at the prestigious program, it couldn’t help him overcome the pressure of performance. This reality made space for other team members to hone and showcase their skills. 

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After his time at Notre Dame, Joe used the lessons learned with the Irish to fully commit to his new role in San Francisco, putting in countless hours to learn plays, understand scenarios, and prepare for anything his team encountered on the field. 

He credits his 49ers mentor Bill Walsh with cementing this work ethic for him and pushing the idea of preparation over talent.  

“When I left Notre Dame, we’d won a National Championship. We’d won three Bowl games. I thought I was pretty well prepared,” explains Joe. “[Bill] woke me up, and really showed me how to get prepared, how to prepare to be perfect every day.”

As Walsh told him, “You’re not going to be perfect every day. If you just want to be mediocre, and you don’t quite make mediocre? You won’t be on this team very long.” 

Joe took the advice to heart, cultivating a work ethic that would maximize his chance of success over 16 seasons on the field, and well into his second act as an investor. 

2. Get the “me” out of “team"

In the startup world, Joe credits the fastest-growing companies with possessing not only talent, but an understanding of what’s expected, and a willingness by founders to lead from within and improve themselves as a means of furthering the team’s goals.

“There is a ‘me’ in ‘team,’ unfortunately, and there shouldn’t be.” Joe cautions that self-interest in a team environment can become problematic. Instead, leaders should focus their efforts on the types of improvements that will move the whole team forward.

He encourages leaders instead to ask, “What can I do today to make myself better that will, in turn, make my team better? It takes an individual effort, but working with others doing the same thing you’re doing.” 

This approach to improvement matters most when things don’t go as planned. Often, mistakes are what you make of them and how you react can dictate how much impact they have on your outcome. Throughout his football career, Joe gained his reputation for keeping his head and staying rational, even when the chips were down. 

“What happens when [someone] makes a mistake? How do you treat him?” In his seasons on the field, Joe cultivated a practice not of criticism, but correction. “Try to help them. I can’t yell at someone out there... for a mistake, because you know you're bound to make one, too.” 

In this respect, the role of QB is analogous to a coach or CEO, says Joe. “It’s up to the coach to teach the players what he is expecting of them.”

While it’s not the role of a CEO to steer every individual decision, they are there to act with a watchful eye to identify and correct mistakes along the way. 

Just like a QB on the field, as CEO, “Everyone looks at you when disaster happens.” 

Knowing how to respond to and learn from these moments makes a difference. 

3. Fail fast and move on

In sports and business, adversity often provides our greatest source of motivation. While success is sweet, our failures improve our game and inform our future decision-making which leads us to better outcomes over time. 

The secret to getting the most out of failure, says Joe, is to “fail fast.” In other words, when issues arise, take the lesson without dwelling on the mistakes. 

“Concentrate on what’s ahead of you. Learn and get back to being yourself, because the more you dwell on it, the harder it is to work at the level you want. It becomes a habit.”

Whether on the field or off, the hits will come. Rather than let them slow you down, Joe experienced these moments as fuel.

“I felt like I was in the game once someone knocked me on the ground.” Joe explains that he learned to seek out this experience as a way to get into the game, joking, “I should have had somebody hit me on the sideline.” 

Moments of adversity can be harnessed to intensify your energy, gain motivation, and allow you to focus on the critical aspects of success. Taking risks and “getting hit early” doesn’t have to be an obstacle if you accept these experiences with the right mindset.

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