Chapter 4
The CEO Job Isn't What You Think It Is
Most entrepreneurs start businesses around their passions without thoroughly analyzing market opportunities. While this passion helps overcome initial barriers, growing companies require founders to shift from hands-on work to leadership responsibilities-a transition many founders find deeply disappointing.
As Moz grew, Fishkin spent progressively less time doing hands-on SEO work he loved-dropping from 20% to sometimes just 5% of his time. Instead, his days filled with recruiting, fundraising, presentations, negotiations, product planning, and countless other CEO responsibilities. The myth of "founding a startup so you can do what you love" crumbles under the weight of organizational demands, as employees, customers, investors, and community members all rely on you to handle increasingly complex responsibilities.
Building a great startup requires developing proficiency in numerous business functions through what the industry calls "muddling through"-a painful cycle of failure, learning and repetition. This six-step process involves: 1) Realizing (often too late) what's holding your team back, 2) Attempting various solutions, 3) Determining most attempts have failed, 4) Finally experiencing some breakthrough success, 5) Discovering unintended consequences of your solution, and 6) Either settling for partial implementation or abandoning the approach entirely. This messy learning process replaces the formal systems that established companies take for granted.
Effective leadership means knowing when to delegate and when to dive deep yourself. Great entrepreneurs must shift from doing what they love to enabling others and solving problems that block progress. For those who embrace this reality, the CEO role becomes rewarding as an enabler who helps scale achievements far beyond what they could accomplish alone.
Unless you love managing people, handling crises, and constantly communicating vision and strategy, being a CEO won't let you do the work you love. Instead, reset your passion from "doing this work" to "creating this change in the world" to align expectations with reality.
Chapter 5
Why Pivoting Is Vastly Overrated
Despite Silicon Valley mythology celebrating the pivot as a fundamental startup right, Fishkin argues this strategy is vastly overrated. Among thousands of successful startups, only a few dozen famous pivots (like Slack, Twitter, and Pinterest) exist. Pivoting means things have gone terribly wrong, as it's typically easier to improve execution than completely change direction.
The cost of pivoting is dangerously underestimated. While execution naturally improves over time through learning and refinement, changing markets means abandoning hard-won customer insights and starting over with acquisition. Switching products discards months or years of validation work, customer relationships, and influencer connections. Even changing business models requires significant energy to migrate existing customers.
Moz succeeded by selecting a growing field (SEO) when few competitors existed, then iteratively improving rather than changing fundamentals. This approach allowed them to overcome initial mediocrity in both blogging and software through persistent refinement over years. Fishkin spent years refining his blogging skills, publishing over a thousand posts before achieving consistent readership. Similarly, Moz's initial subscription tools were barely worth the price, but through persistent improvement in development, engineering, and design, they transformed into valuable software with high customer lifetime value.
Rather than believing execution is everything, Fishkin suggests you can win by being the tortoise-selecting the right race and route, then consistently improving in a less crowded space. He offers four unconventional suggestions for entrepreneurs selecting markets and ideas: 1) It's acceptable to pursue smaller markets where you have unique knowledge rather than chasing venture capital and unicorn status; 2) Great products often evolve from mediocre beginnings through iteration, humility, and survival; 3) Target markets with incumbent solutions that are hated by customers, unable to evolve, protected by advantages you can overcome, or still in early stages; 4) Use keyword research tools to uncover untapped opportunities by examining problem-indicating searches.
Chapter 6
Your Startup Will Inherit Your Strengths and Weaknesses
Companies inherit their founders' attributes-both good and bad. Fishkin illustrates this with examples like Amazon reflecting Jeff Bezos's logistics passion alongside his thriftiness with employee benefits, Craigslist mirroring Craig Newmark's innovation sensibility and inclusivity, and Slack embodying Stewart Butterfield's focus on visual design and user experience. These founder traits become permanently embedded in organizations while supporting team attributes fluctuate over time.
Fishkin explains that Moz has always excelled at marketing but struggled with creating high-quality software-a direct reflection of its founders' backgrounds. While he and his mother Gillian had strong marketing skills, neither had formal programming experience. Even with balanced teams, founders' attributes become permanently embedded in the organization through their biases, business structure, recruiting practices, resource allocation decisions, passions, and blind spots.
This became painfully evident when Moz built its first web index in 2007-2008 with programmer Ben Hendrickson. Despite launching successfully during the 2008 financial crisis and achieving profitability, the project faced challenges when Ben and his team eventually left the company. Despite hiring numerous engineers and investing heavily, Moz struggled to maintain momentum with their link data over the following five years, falling behind competitors-illustrating how a founder's weakness (in this case, Fishkin's lack of engineering expertise) can become the company's weakness.
Fishkin explains that founders' perceptions of what's "hard" versus "easy" in business directly reflect their personal strengths and weaknesses. While conventional wisdom suggests hiring to compensate for weaknesses, Fishkin offers three crucial caveats: 1) Without domain expertise, you'll struggle to identify, recruit, and manage talent in that area; 2) Founders' weaknesses become embedded in company DNA as "debt" that requires significant effort to fix; 3) Relying on others to cover your weaknesses creates vulnerability when those people leave.
Smart organizations craft business models, team structures, products, and marketing channels that leverage founders' strengths while minimizing weaknesses. Moz did this unintentionally but effectively by aligning Fishkin's community-building talent with a business model to match.
Chapter 7
The Venture Capital Game Is Rigged Against Most Founders
Fundraising appears glamorous-press coverage, congratulations, competitive advantage, better offices, higher salaries-but Fishkin warns it can be disastrous if your business doesn't align with the venture model. While acknowledging that venture capital made him a better entrepreneur, his enthusiasm for raising money has diminished over time due to the odds and costs involved.
Founders mistakenly believe investors share their alignment in outcomes, but reality differs. While investors genuinely support founders initially, their incentives shift based on your performance versus other portfolio companies. Fishkin outlines the brutal math: out of ten investments, five will fail completely, three return insignificant amounts, and just two will generate most returns.
The startup failure rate is staggering-30-40% fail completely, while 95% fail to deliver expected returns to investors. VCs raise money from limited partners (LPs) like wealthy individuals, pension funds, university endowments, and billionaires, promising to beat market returns with a target of 12% annual growth. Only 5% of venture firms actually succeed at this goal. The math requires enormous outcomes from a tiny fraction of investments.
The venture capital model requires absurdly successful outliers to work. Fishkin illustrates this with a hypothetical "Scorpio Ventures" with a $400M fund. Even if they invest $15M in a company that sells for $450M (10x growth in two years), they'd only get $112M back-impressive but far short of the $1.2B needed to hit their 3x fund return target. This creates misalignment: VCs might block a $450M acquisition that would make founders wealthy because it barely moves the needle on their fund's returns.
The venture path is only for those willing to take massive risks for unicorn outcomes. The timeline is getting longer too-the average time from funding to exit increased from 3.1 years in 2001 to 6.8 years by 2014, with successful IPOs taking an average of eleven years from founding.
Chapter 8
Most "Successful" Startups Don't Make Their Founders Rich
Despite founding a multi-million dollar company, Fishkin reveals he doesn't have the wealth many assume. With about two years' savings, no car ownership, and a comfortable but not extravagant lifestyle, he challenges the startup gold-rush mentality. While his $220,000 salary provides freedom, startup success rarely equals instant wealth.
Most startup founders earn below market rates during their company's riskiest years, with wealth distribution heavily favoring the very top performers. Fishkin's own earnings at Moz consistently fell below Seattle's average tech salaries from 2001-2015. While founders initially own 100% of their company, fundraising divides shares into common stock (founders), preferred stock (investors with special rights), and stock options (employees).
The fundamental challenge: private company stock has theoretical value but remains illiquid without willing buyers. Unlike public companies with transparent pricing and regulated information disclosure, private stock sales require board approval and face numerous restrictions. Investors typically discourage founder stock sales, preferring to keep founders "hungry" for an exit. Even as CEO of a successful startup, founders can't simply raise their own salaries without board approval, as compensation is tied to market averages.
Founding a startup means sacrificing certainty-taking below-market salaries and basic benefits in exchange for the slim chance your company will survive and eventually make your stock valuable. Despite popular narratives focusing on outliers like Zuckerberg, most startups fail entirely, and even successful ones take much longer to exit than commonly believed. Moz itself, after thirteen years, remains a startup without having returned money to investors or employees.
There are better reasons to start a company: the freedom to determine what you work on, who to hire, and how your organization operates; the chance to share an idea or mission with the world; and the opportunity to dramatically accelerate your career path by demonstrating strategic vision, execution ability, and leadership skills. Just don't go in blinded by money-most of the time, startups are a comparatively poorly rewarded labor of passion.
Chapter 9
Build Marketing Flywheels, Not Growth Hacks
In early 2009, despite the recession, Moz was thriving after launching a successful link index tool. Needing capital to expand their data set against potential competitors, Fishkin spent months pitching over forty VC firms without success. Instead, they turned to growth hacking with the help of UK-based Conversion Rate Experts.
Their brilliant process involved interviewing different user types (paying subscribers, former customers, and community members), identifying objections to signing up, and designing targeted messaging. This led to two major initiatives: a redesigned landing page that doubled conversions, and an email campaign offering a $1 first month subscription to their 120,000+ community members.
While the landing page improvements created lasting value, the email "growth hack"-despite bringing in 5,000 new subscribers and generating an estimated $1 million in revenue-ultimately proved problematic. These promotional subscribers had much higher churn rates, the team became addicted to finding the next "hack" rather than making long-term investments, and repeated discounting trained customers to wait for sales rather than paying full price.
Great marketing isn't about chasing the latest hack-it's about building powerful, ongoing processes that consistently attract the right audiences. Fishkin visualizes this as a flywheel that stores rotational energy and provides consistent output. At Moz, their flywheel was powered by content that SEO audiences discover through search engines, social media, word of mouth, and other channels. This system drove millions of visitors and thousands of free trials monthly, but it required immense initial energy.
For five years, Fishkin blogged almost nightly, creating diverse content that initially reached just dozens of people. Gradually, amplification through links and shares improved their search rankings, driving more qualified visitors. Interestingly, their data revealed that visitors who engaged with their site twelve or more times before signing up stayed subscribed for 14+ months versus just 4 months for immediate converters. This insight shaped their approach: don't rush conversions, but build relationships through education and trust.
The best time to deploy a growth hack is when it addresses a specific friction point in your marketing flywheel. Your marketing approach should be unique to your skills and audience, with any "hacks" serving your overall flywheel rather than replacing it.
Chapter 10
Real Values Cost You Money (But Pay Off Long-Term)
My friend Rob Ousbey once proposed a brilliant idea to make Moz millions by requiring phone calls to cancel subscriptions instead of allowing one-click cancellations on our website. Despite data suggesting this would significantly reduce our 8.5% monthly churn rate, I refused because it violated our TAGFEE values-particularly empathy. As I told him, "they're not core values if you're willing to sacrifice them in exchange for money."
Values force hard decisions and can work against short-term growth, but they provide enormous intrinsic and extrinsic benefits over time. At Moz, we use TAGFEE-Transparency, Authenticity, Generosity, Fun, Empathy, and the Exception-as a litmus test for all decisions. These values began in 2007 after reading Jim Collins's "Good to Great," which identified shared core values as a characteristic of great companies.
Values-driven organizations benefit from the magic that comes from having the right people who share common values. The common mistake is believing recruitment can be separated from values alignment. As Jim Collins explains, "you cannot 'set' organizational values, you can only discover them." You can't install core values into people-instead, you must find people already predisposed to sharing them.
It's tempting to overlook values mismatches when an employee produces high-quality work or has skills that seem irreplaceable. But every time we've done this at Moz, it's backfired. Sometimes the damage is minimal, but other times keeping someone around despite proven values conflicts wreaks havoc on morale.
Values fail in three common ways: when they're seen as mere platitudes not consistently enforced; when they're created just for recruiting rather than being principles you'd uphold despite financial disadvantages; and when they're not explicitly publicized, forcing employees to discover them through trial and error. Real values have costs-they're difficult to embody and will sometimes conflict with making money.
While shared culture and values are crucial, they must not be confused with uniformity. Startups desperately need diversity-both sociological diversity (different backgrounds, ethnicities, ages, genders) and experiential diversity (different thought patterns and professional experiences). The key is finding people who share your ethical beliefs and operational values, not people who look like you.
Chapter 11
Truly Understanding Your Customers Requires Extreme Measures
Jason Fried's advice about solving your own problems gives you a head start on delivering breakout products, but Fishkin learned the hard way that assumptions need validation.
In 2011, he conceived "Moz Analytics" based on his theory that siloed marketing practices would merge into a single function. After two years of development plagued by delays and feature cuts, they finally launched in November 2013 to 90,000+ interested prospects. The results were disastrous-only 2.3% converted to paying customers, who then churned faster than with their previous product.
They failed on multiple fronts: building a massive product all at once instead of iteratively, releasing a buggy product due to pressure despite poor customer testing, and worst of all, basing everything on an unvalidated theory that marketing specializations would converge (they didn't). Instead of spending time with customers to validate assumptions, Fishkin spent it with designers and engineers dreaming up features.
In 2012, after a few whiskies in Philadelphia, Wil Reynolds (founder of SEER Interactive) and Fishkin hatched an unusual plan-they'd each take a week off to inhabit the other's life. The following October, they swapped houses, email logins, passwords, and responsibilities.
The experience proved intensely challenging but rewarding. Managing someone else's email alone was overwhelming-researching unfamiliar people, learning about ongoing projects, contacting Wil's coworkers for context, and exercising constant judgment. Fishkin completely immersed himself in Wil's life-waking early despite being a night owl, attending his scheduled meetings, learning SEER's processes, and even handling an employee's resignation notice.
This experience transformed his understanding of customer needs. He discovered that SEER consultants constantly validated data points manually before trusting tool results and would happily switch between specialized solutions without loyalty to any single platform. The all-in-one tool approach he'd assumed was valuable was being dismantled before his eyes.
To truly understand your customers, you need to know them as people, not just "personas" or "sales targets." When teams rely solely on user interview data or reviews, we tend to create features barely better than established processes. This happens because we're trained to make decisions based on numbers rather than empathy.
Chapter 12
Losing Focus Nearly Destroyed Everything We Built
The most awful day Moz ever experienced was August 17, 2016, when they laid off 59 of their 210 employees, shut down two products, and abandoned their strategy of the previous two and a half years. This devastating event came as a complete surprise to most of the team, and their lack of transparency leading up to it is Fishkin's greatest regret. How did they go from seven years of 100% growth to layoffs? The answer: lack of focus.
After raising $18 million in 2012, Fishkin foolishly believed they needed to spend quickly to accelerate growth. Despite their board not pushing for this, he diverted attention from their core business to pursue a broader product suite. They tried to follow companies like 37signals and Atlassian by expanding into multiple product lines, worried that focusing solely on SEO would limit growth.
By mid-2016, they had eight different products and services, including two conferences. Selling eight different things proved vastly more challenging than selling two or three. Every team was spread thin, competing for resources and attention as they grew from 125 to 220 employees in just two years.
In June 2016, their CFO Glenn and Fishkin discussed Moz's financial situation. Despite historically operating profitably, they were now burning cash at an alarming rate. Understanding revenue and expenses had become complex with eight different revenue sources, each with different models and cash-flow patterns. Every product was growing but missing projections, with an uncanny correlation suggesting each new product subtracted growth from every other offering.
Following the layoffs, Moz achieved its first cash-flow-positive month in four years by November 2016. Though painful, without the layoffs Moz might not have survived at all.
Looking at Moz's financial history from 2007-2017 reveals that post-2013, their growth slowed dramatically despite massive spending. Between 2012-2016, they consumed over $35 million in venture capital and debt while growing much slower than in previous years.
The fundamental lessons were clear: 1) Focus on subscriber retention over customer acquisition; 2) Multiple products dilute your brand; 3) Organizations struggle with numerous priorities just as individuals do with multitasking; 4) Few companies are truly best-in-class at everything they do; and 5) Growth becomes exponentially harder as companies scale.
For early-stage startups, the mission is clear: find product-market fit, then scale. But after achieving fit, the mandate becomes "find growth through any means possible" because growth drives valuations, talent attraction, press coverage, and potential exits. This mindset leads to dangerous thinking like "Our core product is growing, but I bet we could grow even faster if we..." Far wiser, though requiring more discipline and patience, is focusing on becoming the best in the world at one thing and letting other growth strategies wait until achieving massive scale.
