Ep. 85 - What it Takes to be a Great Entrepreneur During the Pandemic: Always be Sweating, Always be Learning, & Always be Trying with Tim Guleri

January 12, 2021 Strategic Momentum

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Ep. 85 - Tim Guleri from Sierra Ventures Strategic Momentum Podcast

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We are still in the midst of the pandemic, but these trying times have also led to an increase in entrepreneurial activity and opportunities.

According to a Wall Street Journal analysis, “Americans are starting new businesses at the fastest rate in more than a decade.” The Foundation for Economic Education even cites that the pandemic offers a moment ripe for ‘creative destruction.’

That’s certainly not surprising for Tim Guleri, who has been knee deep in the startup world for much of his career. As a Managing Partner at Sierra Ventures, a Silicon Valley-based early-stage venture firm investing globally with a focus on Next Generation Enterprise and Emerging Technologies, he knows all too well the journey and evolution of successful entrepreneurs. Over his 18-year career in venture capital, as well as being a former serial entrepreneur himself, he has developed an inherent understanding of those critical traits aspiring and current entrepreneurs need to possess to build businesses that thrive.

But he didn’t set out to be an entrepreneur. In fact, it was his curiosity and desire to ‘Alway be Trying’ that led him down the path of expanding his skill sets, experiences, and, ultimately, his career.

In this episode, Tim shares

How perspiration and inspiration got him to where he is today
Traits of elite entrepreneurs and how they have evolved over the years
What it takes to be a great entrepreneur, break through the noise, and create a sustainable business during a global crisis

Developing a Growth Mindset: Always Be Curious, Don’t Fear Failure, and Learn Constantly

Tim grew up in India, where his home environment fostered exploration, instilled a work hard ethos, and encouraged him not to fear failure. In fact, he did theater, played soccer, and even entered a singing contest; he wasn’t singularly threaded towards academics. And these lessons he learned in his youth have been a critical part to his approach to life and business.

He came to the U.S. to get a Masters in Industrial engineering and robotics, and was excited to explore the opportunities that the states could offer. However, when his scholarship got cancelled, he had to find a way to support himself so that he could finish his degree — and fast.

That led him to finding a summer job in California going door-to-door selling books that were half biblical content, half math and science... and he had to do so in 107 degree weather with a 40 pound bag on his back.

However, that experience was transformative for Tim; he learned a core skill that has been fundamental to his career success ever since, but wasn't something that formal education ever taught him or exposed him to: sales. He was so good at selling, in fact, that he made Quota Club, a group of top achieving salespeople.

After graduating from school, Tim got a job at a semiconductor company, which was more in line with his academic background. However, as someone who was (and still is) naturally curious, it wasn’t surprising when the entrepreneurial bug eventually hit him.

Tim responded to an ad for an engineer in San Jose’s The Mercury News. That serendipitous action set his entrepreneurial career in motion. He joined Scopus as employee number six, starting out as an engineer. But he also loved customer conversations, triggering a pivot into sales engineering and then sales, which he excelled at.

Tim achieved entrepreneurial success with Scopus, as they eventually went public and were acquired by Siebel Systems for $800M.

But Tim had higher aspirations still. He decided that he wanted to be CEO of his own company. Given that Tim had built functional skills in other areas while at Scopus, including product management and marketing, he was able to get a big-picture view of how the whole organization ran. That career journey gave him the confidence and knowledge of what worked and what didn’t of which he took with him when he started Octane in 1996.

Tim eventually sold the company for $3.2B. From there he made another pivot into venture capital, and he’s been at Sierra Ventures now in their 38th year.

Evolution of Entrepreneurs - From Linear and Sequential to Parallel-Pathers

Tim shares that, in the past, becoming a CEO involved learning every function within a company sequentially because you had to be narrow and deep to “truly learn all that you needed to learn to be that well-rounded executive.” But that took a decade.

But today, elite entrepreneurs are coming out with these well-rounded backgrounds much earlier as a result of being able to educate themselves through the scale and scope of resources available; they are parallel-pathing their learning and subsequently accelerating their knowledge and abilities to be the best.

Having worked across multiple functional roles himself, Tim also believes that both those right brain and left brain oriented skills are vital to entrepreneurs today.

Entrepreneurs During the Pandemic - What Holds them Back and How Great Ones Thrive

Entrepreneurs are a class of people that take advantage of the environment that they are in — and the pandemic is no different. And today’s amazing entrepreneurs are always recalibrating because the world around them is constantly evolving. And during COVID, it literally is. You have to pivot, adapt, adjust, and reflect on what works and what doesn’t. As Tim says, it's being comfortable with changing the playbook but also focusing on creating that solid financial foundation.

But what holds many back is that they are thinking too myopically and not thinking through what the end state of their business will be. In the end, every company is a financial product

Creating that startup momentum also has to come from a truly authentic place. As Tim mentioned, he looks for that core reason as to why someone would want to start their company in the first place — what is the burning desire and what need are they truly solving for? That passion, purpose, and ability to tell a compelling story and paint the vision is key.

Because, as an entrepreneur, you're convincing others to come on the journey with you. And as a leader, self-awareness and humility are critical factors because you need to know what you are good at and what you’re not, so it’s important to surround yourself with those who can compliment you. At the end of the day, it’s the collection of people that drive the company forward — not a single person.

Career Advice

Career success has to do with having fulfillment and joy in what you do every day.
The biggest skill that you can have in life is knowing how to read people - the ability to read, the authenticity of a person, finding what the positive attributes are, somebody that you can work with or work for. That’s a skill that stays with you for life.

Key Takeaways

Always be sweating - work hard, always be learning - have a super curious mindset, and always be trying - be open to constantly trying something new.

You have to constantly be reinventing yourself as an entrepreneur because your tools and skills can get dull.
It’s critical to be okay with failure and then be able to pick up and go because in the end you’ll learn new skills.
Having a variety of experiences particularly across a range of functions is incredibly valuable. It enables you to see how an entire organization operates.
Parallel pathing to get the big-picture and being well-rounded in the end is paramount. These traits of elite entrepreneurs because it is now easy to self-educate and test and learn to see what worked and what didn’t.
There are three key factors aspiring/current entrepreneurs to consider during these COVID times.
- “Whatever idea or product that you're building, make sure it's an aspirin, not a vitamin.” This has to be a product or service your target audience has got to have otherwise the business won’t work. It has to have a very fast return on investment for a customer that buys your product.
- Make sure you're in a market that is growing and is large so that by definition, you could build a large company.
- Always focus on fundamental business milestones and metrics. For example, if you are a software as a service company, it's your recurring revenue, your gross margin. Focus very cleanly on fundamental business metric metrics that matter.
Don't think myopically. Think about what market segments you're building your company for and are those segments going to attract investors? If so, why? If not, why? Think about how you milestone the business to ultimately create a great financial product, which then can be hopefully taken public and survive and thrive after that.

In order to breakthrough and gain the traction you are looking for as an entrepreneur, you need to be authentic in the pursuit of your idea and great at storytelling because you have to be effective at convincing people on why they want to come on the journey with you.
Be smart about the resources you are going to consume to get the business off the ground so that you build an efficient company over time.

Remember as an entrepreneur, the company is not a personality - it’s not about YOU. It's actually the collection of the people that drive the company forward. Founders that are self-aware and humble attract a team.
While companies that revolve around a single person can succeed they have a higher probability of failure.
The best entrepreneurs not only possess the hard skills (they are foundational) but also that next layer of soft skills (e.g. communications, EQ) which are necessary to build the business to where it needs to be. That combination makes an A-player.
The trait of self-awareness in entrepreneurs is critically important because no one person can have all the knowledge or perform 100% on every dimension.

Connie Steele I Future of Work Expert