10 Lessons From a Decade in the Startup Ecosystem
A first-hand hard learned lessons and observations.
Depending on your perspective, a career in startups can be simultaneously draining and fulfilling. By "fulfilling," I mean not only the financial rewards but also the rapid pace of achievement and learning. Such accelerated growth is rare in conventional corporate settings.
Over a decade ago, I took the plunge into the startup ecosystem and haven't looked back. In my early years, job security took a backseat to intellectual curiosity, skill development, and the allure of new challenges. These priorities became the foundational elements for my enduring engagement with startups.
Today, upon reflection, I realize the breadth of valuable experiences I've garnered across diverse startups in multiple industries and regions.
That's why in this post, I've chosen to share my insights, lessons, and observations from working with startups at every stage, from Seed to Pre-IPO. Some of these lessons come from direct exposure, while others have been curated through long-term observation and in-depth discussions.
Lets dive in:
Lesson #1: Learn To Be Scrappy
Being scrappy in a startup environment involves maximizing limited resources, adopting agile methods, and discovering unconventional solutions. The ability to adapt and optimize resources can often make the difference between success and failure, especially given time and resource constraints. Scrappiness isn't about cutting corners; it's about optimizing for efficiency and cost-effectiveness.
So, here are a few tips if you want learn to be scrappy:
Prioritize: Keep your focus sharp on what truly matters. Don't dilute your efforts by spreading yourself too thin.
Do More With Less: Utilize existing resources creatively instead of impulsively adopting the latest tools.
Bootstrap: Stretch your existing resources as far as they'll go before seeking external funding or help.
Learn Fast: Implement quick feedback loops. Mistakes are fine as long as you learn from them swiftly.
Automate: Automate repetitive tasks whenever possible, freeing up time for higher-priority activities.
Lesson #2: Skills Progression is Inevitable ( * if you want to progress )
The continuous skill development is one of the reasons I've always enjoyed working with startups. Don't assume your role will remain static; this is especially true in Seed or Series A startups, where the pace is fast, and pivots are common.
Here are a few examples from my career and how my duties evolves over time
Company #1
Started as an SEO Lead → The company needed someone to build their non-paid channels from the ground up.
Added More Channels → Well, SEO was just the beginning. Later, I took on more initiatives around CRM and SEM, which gave me full-suite marketing exposure.
Ventured into Marketing Analytics → Gradually, I started to delve deeper into data to understand the true impact of all marketing experiments and campaigns.
Data Tracking & Product Analytics Integration → Measuring your own channel performance is important and often a constant issue, especially the attribution piece. That's why I took on additional work to set it up correctly. Additionally, I wanted to understand how my channels impact the entire business end-to-end, so I collaborated with the data team to figure this out.
Company #2:
Started with Retention → The main issue was understanding why users didn't stick around. The churn rate was alarmingly high.
Moved to User Activation & Onboarding → Retention was just one signal. To get a fuller picture, I needed to understand the entire customer journey, from acquisition to onboarding and activation, all the way to habit formation. This led me to work more closely with the product team.
Participated in Product Roadmap → Through our collaborative work, we identified numerous opportunities that became part of the company's overall roadmap. I led the growth team and executed experiments to influence key metrics positively.
Built an End-to-End Growth Model → Having gained insights into the levers affecting acquisition, retention, and monetization, it became clear that the company needed a high-level data model to understand where to focus efforts to meet business targets.
Lesson #3: Don't Overlook Founder-Employee Fit
This lesson became increasingly evident to me while working with later-stage startups. In smaller teams of around 10 to 20 people, daily interactions with founders are common. But as the organization grows, surpassing 100 employees for example, the structure evolves. Departments form, each led by their own leaders, and the degree of direct engagement with the founders often diminishes.
However, even if you're not directly interacting with the founders, their influence permeates the entire organization. The company culture, strategic direction, and overall ethos usually emanate from the top. Therefore, it's crucial to assess how well your own values and work style align with the founders, even if your interactions with them are limited.
Being in sync with the founders' vision and methodology can significantly impact your job satisfaction, performance, and even your stress levels.
In growth roles like mine, this fit is even more important because my initiatives are often directly tied to the company's core objectives, which are set by the founders.
Lesson #4: Your Try & Fail Rate Needs to be Hsigher
n the startup landscape, it's not enough to rely on tried-and-true methods for growth. Iteration is the name of the game. While failing often may feel demotivating or risky, it's important to see each failure as an opportunity for learning more about your customers, business model, or market.
Real-World Applications:
Experimentation Program: In teams that I lead, I embed a KPI that mandates a failure rate above 80%. This means that if we run ten experiments, we should expect to fail in eight of them. Failing isn't the issue; not learning from it is.
Marketing Channels: Sticking solely with what's working now is not a long-term strategy. Relying on a single channel will inevitably lead to saturation, causing growth to plateau. It's crucial to diversify and take calculated risks in channel experimentation to maintain and amplify growth.
Key Takeaways:
High failure rates are not a sign of ineptitude; they're an indicator of rigorous experimentation and learning.
Rigidly sticking to current successful methods without exploring new avenues limits potential growth.
Adopting a mindset that sees failure as a learning opportunity rather than a setback allows for a more agile and adaptable strategy.
Lesson #5: First-Principles Thinking is a Game-Changer
First-principles thinking is a method of problem-solving that involves breaking down complex challenges into their most basic, fundamental elements. Once these foundational truths are identified, they are reassembled to create new, innovative solutions.
Elon Musk's work with SpaceX and Tesla serves as prime examples of first-principles thinking in action. At SpaceX, instead of accepting the high cost of existing rocket parts, Musk broke down the components to their raw materials to understand the foundational costs, allowing for more cost-effective manufacturing. Similarly, at Tesla, first-principles were applied to rethink battery technology and production from the ground up, rather than making incremental improvements on existing tech.
How I`ve used in real-world example?
I've applied first-principles thinking to tackle customer churn in one of the startups. Instead of using existing retention strategies, I broke the issue down to its basic elements: why customers joined, why they leave, and what value they seek. By isolating these fundamentals, we developed a highly personalized retention plan that reduced churn by 10% -15%.
In another instance, I used first-principles thinking to reimagine our product development pipeline. Rather than adhering to conventional agile methodologies, we deconstructed what "efficiency" and "speed" really meant for our specific context. This led us to create a hybrid development framework that increased our development speed 3x while maintaining quality.
Lesson #6: Don't Work Solely on Easy Problems
To rapidly advance in any organization, there's a common tendency to tackle multiple low-impact issues to show progress. This approach is not necessarily aligned with business growth, especially in startups. I've learned to balance problem-solving using the "Rocks, Pebbles, and Sand" framework. As a growth leader, I prioritize quarterly planning and categorize tasks as follows:
Rocks: At least one high-impact problem with significant customer and business implications.
Pebbles: New features, marketing channels, etc.
Sand: Multiple minor improvements, like data tracking issues etc.
Over time, this approach has helped me focus effectively and prioritize accordingly.
Lesson #7: Ego Will Not Help You in The Long-Run
This specific point, is the one I`ve seen so many times in almost every startup stage company i`ve been. But I will break my observation into 2 particular areas:
During early stages startups, individuals closer to the founders tend to develop outsized egos, thinking they have all the answers.
In later stages, when the company has grown in team size and is more structured, featuring a C-suite and organized onboarding and training processes, most employees don't have direct access to senior leadership. In this context, direct managers, often seasoned professionals from well-known companies, become the primary source of authority. They set the rules, serve as examples, and their voice carries the most weight.
An interesting dynamic I've observed is that department heads or managers often become uneasy when a founder seeks feedback or conducts private sessions with employees below their level.
To succeed long-term in a startup and foster a healthy environment among both direct and indirect peers, it's imperative to initiate change starting with yourself. This involves eliminating ego from the equation.
It's crucial to remember that the company's mission and goals are larger than any one individual, particularly in startups. Discarding the "I'm the most important" mindset is vital for sustainable success and growth.
Lesson #8: Engage with Business Fundamentals Early On
I used to neglect the business side, assuming that senior management would handle it. Today, I urge everyone to get their hands into the financial dynamics of their startup. Understanding the business goes beyond market dynamics and extends to:
Current P&L: A broad understanding of the business's financials, particularly at the revenue level.
Team's Financial Contribution: Monitoring your team's impact on the financial health of the company.
Resource Allocation: Knowing what the company can afford in terms of hiring and tooling aids in realistic planning for expansion and investment.
Lesson #9: Prepare For a Rollercoaster Ride
Startups aren't for those seeking stability or a monotonous job. There are three pillars I focus on when navigating this unpredictable landscape:
Expectation vs. Reality
While many enter the startup world with dreams of swift success, the reality is that there will be unforeseen challenges, market changes, and hurdles. Recognising this early on helps set realistic expectations.
Startups often envision rapid growth and market domination, but the path to success is rarely straightforward. By understanding that challenges and setbacks are a natural part of the journey, startups can approach them as learning opportunities rather than discouraging roadblocks.
Emotional Resilience
Entrepreneurs experience a wide range of emotions, from the euphoria of hitting milestones to the stress of facing setbacks. Recognising and accepting these emotional swings is the first step in managing them.
It's easy to get consumed by the drive to succeed, leading to long hours and little rest. However, understanding one's limits and ensuring regular downtime can prevent burnout and maintain consistent performance.
Adaptability is Key
The startup world was ever-changing. Instead of resisting it, I embraced change, seeing it as an opportunity to refine my strategies.
I made it a habit to seek feedback regularly. Whether from customers, my team, or other stakeholders, their insights were invaluable, helping me align with market needs and adjust my strategies accordingly.
Lesson #10: Don't Skip To Switch Off
When I first embarked on my startup journey, I believed in the mantra of "hustle all the time. I thought that the more hours I poured in, the quicker I'd see success. But over time, I realised this constant grind was not only exhausting but also counterproductive. I learned the hard way that without taking breaks, my creativity and problem-solving abilities diminished. Time off allowed me to step back, refresh, and return with a clearer perspective. It wasn't about being lazy; it was about being effective.
As a leader, I realised that my actions set the tone for my team. By not taking time off, I was indirectly promoting a culture of overwork. When I started to prioritize my well-being, it signalled to my team that it was okay for them to do the same.
Final notes
Concluding this article, I strongly believe that everyone should seize the opportunity to work for a startup at least once. The experience will expose you to a unique set of challenges and opportunities that you won't find elsewhere. And who knows? Maybe you'll be inspired to build your own startup one day, armed with the invaluable lessons you've learned along the way.