Founder Guides

Riding the waves of entrepreneurship with Guy Kawasaki and Grant McCarthy

OG technology evangelist Guy Kawasaki joined Tidal Managing Partner and Co-Founder Grant McCarthy to discuss the characteristics of remarkable founders and how to navigate the long and exciting journey of being an entrepreneur.

Grant McCarthy

22 Apr 2024 · 9 min read

In the ever-evolving world of technology and investment, where timing can dictate destiny, a spur-of-the-moment encounter between Tidal Managing Partner Grant McCarthy and renowned tech evangelist Guy Kawasaki led to a fruitful dialogue. As Grant recalls, what began as an ambitious plan to host an event during Guy’s visit to Sydney soon faced logistical hurdles reminiscent of the challenges startups often encounter. Luckily, fate intervened, leading to a meeting in San Francisco where, sharing surfboards and experiences, a connection formed. Beyond their love for surfing, Guy and Grant share a keen eye for tech investment opportunities shaped by their respective journeys.

For Guy, it has been marked by his pivotal roles during the early Apple days and advising Canva during their early product development. Grant’s journey to becoming the technologist he is today is equally storied. Amidst the frenetic energy of the dot-com bubble, Grant dove headfirst into the tech scene, joining Yahoo as its 14th Australian employee. He played a pivotal role in shaping the company’s trajectory, working across some of its earliest investments, including industry leaders like Seek and Carsales. At Tidal, he’s backed ventures like Shippit, now valued at $300m and FrankieOne from their earliest stages.

These shared early tech experiences make for a good yarn filled with valuable insights into how to build and grow a tech company, offering a firsthand perspective on what it truly takes to succeed.

The role of luck and timing

Grant emphasises the importance of recognising the “corporate lotto cycle” in startups, where success often depends on fortuitous timing and circumstances. Reflecting on his journey, Guy candidly acknowledges, “Yeah, I worked for Apple. I worked for Canva. I was on the Wikipedia board of directors and a Mercedes Benz brand ambassador. I’m trying to paint this picture, but I really don’t know what the hell I’m doing all the time.” Guy believes that luck isn’t merely a matter of chance but a culmination of factors aligning at the right moment. “It’s not just because you have growth and grit,” he asserts. “It takes luck, and it takes, you know, some teacher in your past, some coach in your past, some mentor in your past. A lot of things have to line up to be remarkable.”

Guy’s journey with Canva mirrors the unpredictable nature of startup fortunes. Drawing parallels to his early days at Apple, he recalls the pivotal moment when Canva’s potential became apparent. His social media manager’s recommendation and personal experience led him to adopt the “Peter Lynch theory” of investing in products he uses. This mix of personal conviction and timing underscores the relationship between luck and strategic insight. Just as luck and timing played a role in Guy and Grant’s meeting in San Francisco, so too do they shape the trajectories of startups—highlighting the importance of seizing opportunities and cultivating meaningful connections.

Remarkable founders know how to “turn and burn”

Luck and timing aren’t the only things that matter; remarkable founders also know how to make good decisions and be flexible when things don’t go according to plan. Guy, the surfer he is, likens this process to the “turn and burn” manoeuvre, which requires founders to seize opportunities, adapt to evolving conditions, and navigate uncertainty with confidence and precision.

As Guy puts it, “As soon as you make your decision, you switch from, is this the right decision to making the decision right?” In the same vein, he elaborates on the intricacies of surfing, highlighting how “you’re trying to sit in the right place, you’re trying to turn at the right time, you’re trying to paddle in the right direction, you’re trying to pop up at the right time. There’s a lot of variables.” Guy emphasises, “That’s what makes surfing so hard... at some level, once you turn and burn and start paddling, it’s all about making the decision. You got to compensate. You got to change. You got to do whatever you got to do. It’s about making the decision right when push comes to shove.”

Grant highlights that unique early-stage challenges, like figuring out product-market fit and scalable go-to-market strategies, can often involve guesswork. “A lot of the time, particularly in the early stage, at the seed stage, you’re guessing a lot of the time,” Grant explains. Grant’s insight adds another dimension to the “turn and burn” approach, underscoring the delicate balance founders must have between intuition and strategy.

You’re trying to align yourself with people you think are quality, people you can work with who will make hard and fast decisions and have a cadence of speed in doing things.

Finding the balance in product development and sales efforts

Every successful startup’s heart lies in a dual focus: building a remarkable product and effectively selling it to the market. As Guy succinctly says, “100% of your focus should be on making and selling it.” Take, for example, the iconic partnership between Steve Jobs and Steve Wozniak, where their synergy in product innovation and sales acumen laid the foundation for Apple’s unprecedented success.

Grant echoes this sentiment, emphasising the need for startups to prioritise product excellence early on. He affirms that startups armed with a remarkable product, addressing a pressing problem across geographies, often find themselves ahead in the sales game. “With a great product that solves a really hard problem,” Grant advises, “you don’t have sales problems.” However, he highlights that the real challenge for startups with a great product lies in acquiring the right sales talent and capabilities to leverage this product advantage effectively. Grant’s insight sheds light on the pivotal role that sales capability plays in translating product potential into tangible business growth.

How Grant and Guy identify founders with promising potential

Having spoken to countless founders over the years, both seasoned investors pay close attention to the founder’s character—specifically their potential to grow and endure the challenges of the startup journey. Grant points out how important it is to understand the founder’s mindset early on, stating, “One of the things that we’ve always tried to do at Tidal is spend as much time with these founders early in their problem-solving product mindset of what and how they’re going to build something.” For Tidal, it’s not solely about assessing a founder’s technical skills or industry knowledge but also about predicting the founder’s evolution as they go on their journey.

Grant explains:

It’s not only how good they are at product or what knowledge they have about the problem, but also what kind of person they will be as they go through that process.

This is at the core of Tidal’s investment principles, primarily driven by our distinctive operator-led approach. Unlike conventional venture capital firms led by investors, being operator-led means your investors are individuals with firsthand experience as founders and builders of tech companies. Tidal is committed to working closely with founders, offering them insights and advice from practical experience rather than mere theoretical knowledge.

Being the right “asshole” leader

Drawing from four decades of frontline experience, Guy asserts his authority on a subject, saying, “I have become an expert in assholes.” He swiftly clarifies, not in the proctology sense, eliciting a chuckle from Grant. Guy distinguishes between two breeds of such leaders: the egocentric and the mission-driven. The former, he elaborates, is consumed by self-glorification, exemplified by an entourage and a penchant for ego gratification.

In contrast, the mission-driven “asshole” is driven by a singular purpose, unyielding in the pursuit of their vision. He cites Steve Jobs as a prime example of the latter, lauding his focus on creativity and productivity over self-aggrandisement. Grant concurs, emphasising the importance of tyrannical focus in realising one’s mission, a trait reminiscent of Jobs’ legendary dedication. Guy reflects on his time working with Jobs, acknowledging the fear he instilled while underscoring his genuine desire to revolutionise the computer business.

Navigating different mindsets and self-belief in leadership

The distinction between growth and fixed mindsets has profound implications for leadership. Guy believes that having a fixed mindset constrains personal advancement and leads to biases hindering company growth. He articulates, “The fixed mindset is the mindset that you believe that you cannot gain new skills, that, if you open yourself up to the vulnerability of learning new things, it may be at one level embarrassing or even worse, it’ll mark you as a failure.”

This mindset often permeates hiring practices, leading founders to favour candidates who mirror their own attributes, potentially limiting diversity and innovation within the team. Fostering a growth mindset empowers founders to embrace continual learning and adaptability. As Guy highlights, “The growth mindset, by contrast, says that you can grow, you can expand, you can learn, you can do things.”

The three common founder mistakes to avoid in early-stage startups

Mistake 1: Hiring biases and lack of diversity

Guy highlights the detrimental impact of hiring biases, particularly when founders gravitate towards hiring individuals who mirror their personas or demographics. He argues that such bias reflects a need for a growth mindset, stifling innovation and progress within the startup ecosystem. Companies that embrace diversity show they’re fostering a mission-driven culture where the focus is on potential hires being part of a solution to a problem.

Mistake 2: Neglecting sales efforts

Another critical mistake is the tendency for early-stage founders to neglect sales efforts, leading to running out of funds. As Guy emphasises, “sales fixes everything.” He cautions against diverting excessive resources towards superficial “strategic” initiatives at the expense of core revenue-generating activities, stating, “When you start throwing around a strategic... you’re full of it. Because you know what? We don’t want strategic shit. We want money. We want sales.” Guy’s insight underscores the necessity of prioritising tangible sales outcomes over abstract strategic pursuits, highlighting the importance of generating revenue for sustaining business growth and viability.

Mistake 3: Underestimating time and effort in feature implementation

The final mistake is when founders don’t understand the complexity and effort required to build their technology. This tendency often leads to overpromising delivery timelines and revenue potential, resulting in disappointment among stakeholders. Guy stresses the necessity of realistic planning and diligent execution to avoid the pitfalls of overcommitment and subsequent under-delivery. Guy jokes, “Whenever a CEO tells me when something will ship and how much revenue will be generated, I add one year to the shipping date and divide it by 100.” Grant adds to this, suggesting, “I would say add a year, double the cost and half the revenue.”

How to win the AI race

To Guy, AI is a transformative force poised to revolutionise the world—a sentiment aligned with Tidal’s thesis. His belief in the transformative power of AI is unwavering, as he asserts, “I think that AI is a bigger deal than mobile phones, Internet, social media, personal computing.” This conviction stems from his extensive experience in the tech industry, where he has witnessed firsthand the profound impact of technological innovations. Amidst the growing impact of AI, Guy emphasises the importance of authenticity and substance, cautioning against the superficial use of AI as a buzzword. “Show me a company that isn’t using AI,” Guy challenges.

“If you’re saying you’re using AI, you better really be using AI in some significant way. You’re not just blowing smoke to increase the valuation of your company. I think when all the dust settles, you know, you cannot bullshit your way out of this.”

Grant, aligning with Guy’s perspective, recognises the increasing ubiquity of AI in everyday business operations. He acknowledges, “The really interesting thing is people are just generally starting to use it in their everyday business for everyday things.” This observation underscores the growing adoption of AI across various sectors, reflecting its expanding role in driving efficiency and innovation. However, Grant emphasises the importance of substance over rhetoric, echoing Guy’s sentiment that mere lip service to AI is insufficient. “You got to look at that and figure out that just saying the words AI is not going to buy you much longer,” Grant asserts. “Show what you’re actually doing with it as a product.”

Both Guy and Grant advocate for a pragmatic approach to AI adoption—one rooted in genuine innovation and tangible impact. Their insights highlight the need for founders and businesses to move beyond buzzwords and focus on delivering real value through AI-powered solutions. As the AI landscape continues to evolve, their guidance serves as a beacon for navigating the complexities of this transformative technology.

The key to navigating different market cycles

In navigating the ever-shifting market tides, seasoned tech veterans offer invaluable insights honed through weathering multiple market cycles, including the dot-com bubble, the global financial crisis (GFC), and the recent COVID-19 pandemic.

Grant talks about the enduring nature of successful journeys amidst fluctuating market cycles. Reflecting on the prolonged timelines inherent in building successful startups, Grant emphasises the futility of fixating on market cycles:

When you start businesses, you are often on potentially multi-decade journeys. So, worrying about where a market cycle is up is out of your control. What you do have control over is your product and your sales.

Guy agrees that market fluctuations are insignificant compared to the laser focus founders must maintain on their companies’ goals. “I don’t care if venture capital is up or down or startups are up or down. All an entrepreneur needs to care about is your company.” His perspective underscores the importance of prioritising your own company over external market forces, regardless of prevailing conditions.

Tips for founders pitching their startups

Guy’s mantra, the 10-20-30 rule, serves as a guiding light for startup pitches. It advocates for ten slides, twenty minutes, and a minimum font size of thirty points. Yet, beyond slide counts and font sizes, Guy addresses a common pitfall among founders: the tendency to ramble instead of delivering a concise pitch.

At the heart of Guy’s advice lies a sense of urgency. Founders, he insists, are not flying lumbering Airbus 380s with endless runways at their disposal; they’re strapped into F-16s hurtling off aircraft carriers, where every second counts. In this high-stakes environment, the opening moments of a pitch are make-or-break. “So that means in the first 15 seconds, explain what the hell you do,” Guy advises. “Because until you explain what the hell you do, nobody gives a shit about your world-class technology or world-class background”.

We’re passionate about backing founders who disrupt markets and build transformative products that shape the future. If you’re working on an ambitious product that has the potential to revolutionise industries, get in touch.

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