Nashawn Chery

How to Fail Successfully at Entreprenuership

Lessons from nearly a decade as an entrepreneur

    The entrepreneurial journey is one that can take you through valleys of challenges and tribulations, but also to peaks never thought imaginable. It’s a journey you have unlimited opportunities to embark on, and painful past failures can be some of the best experiences to improve your odds of success in the future. Most critically, you only truly fail when you officially throw in the towel and never try again. 

    Drawing from my experiences of founding and running two startups over the past eight years, I want to share three pivotal lessons that have not only shaped my entrepreneurial journey, but can also serve as a blueprint for success in the future.

Lesson 1: Find Quick Clever Ways to Test Your Thesis and Assumptions

    Continuous learning and adaptation are critical components of success in the business landscape. To achieve this, it’s essential to identify and address all potentially arguable assumptions your venture is founded upon. In the earliest stages, you must play the roles of a researcher, psychologist, marketer, and data scientist, blending these skills to find the easiest, quickest, and fastest ways to test and validate your thesis.

Here’s a sheet of tools to ‘pretotype’ your ideas defined by Tina Seelig /Alberto Savoia from Stanford [link]

    Using my most recent venture Shea’d as an example, we built tools to help consumers connect with Black-owned businesses. We initially built a mobile application that provided a directory of Black-owned businesses in the Bay Area. With this product, we gained 3k+ downloads, 1300+ newsletter subscribers, and won our first grant. Despite early success, we pivoted to a browser extension due to the pandemic, which proved to be a challenge. The thesis behind the browser extension hinged on the belief that consumers would more frequently choose products from companies that most closely aligned with their values. Instead of running low cost experiments such as providing a concierge service to confirm this, we delved straight into building the tech. We sunk months building the first iteration, and the response was unenthusiastic. 

    In the early stages, perfectionism is your enemy. This is because you are aiming to perfect something that is unproven. Instead, focus on distilling your thesis into quick, low cost experiments formed around the most important core metrics that would validate or disprove key aspects of your business. Speed up the iteration process by debunking false assumptions quickly, to land on a product actually worth perfecting.

Lesson 2: Secure Your First Commitment Quickly

    Attaining your first commitment from customers is critical for validating your product's value. Aim to get your first commitment such as time, reputation, or a first dollar from a customer as swiftly as possibly. The trick here is to engage in research conversations WITHOUT mentioning your product. Identify individuals and customer segments that align with the problem you’re solving or value you are creating. Only once you've confirmed alignment, present your solution and secure a firm commitment. This could be an introduction that leverages the customer’s reputation, a time commitment such as piloting your early product to provide feedback, or a pre-order.

    Plural Policy, a tool to help small companies and nonprofits manage legislation, exemplifies this lesson. Damola, a cofounder, witnessed a real need through early conversations with nonprofit operators. These operators maintained a messy process of tracking legislation progress and managing action items, all on a spreadsheet. The team quickly developed a first iteration, or an MVP, that was slightly better than a spreadsheet. Within months, they secured agreements of $300/month, $1k/month, and $3k/month with a lean, crisp product.

Lesson 3: Build Your Team and Tribe

    Success in entrepreneurship is seldom a solo endeavor. You must  surround yourself with a strong team including a co-founder with who you can be brutally honest with, advisors that form your braintrust to help guide your strategies, and technical co-founders or early hires who share your vision. Most notably, one of the great benefits of failing successfully is you build a rolodex of people that you take with you from one venture to the next.

    Reflecting on my journey, long-term relationships have been integral. To this day, I continue to work alongside some of the same individuals whom I've shared common goals with since freshman year in college. To maintain working relationships and friendships, trust is paramount. To do so, it is important to keep front and center how each person’s individual goals and interests shift during the process of building. You must then trust them to grow and take on new responsibilities of interest, as the organization also grows and expands. Also at times, people outgrow the product they’ve helped build, and that’s okay. Champion the growth. If you truly make a space for people to feel great about doing their best work, when opportunities present themselves, people will often aim to return to spaces where they’ve felt challenged, cherished, and respected.

    In the ever-evolving landscape of entrepreneurship, these three lessons have been instrumental in shaping my entrepreneurial journey. Find innovative ways to test the theses your company is founded on, secure commitments quickly, and build a strong team and tribe. Armed with these insights, you can navigate the challenges of entrepreneurship and increase your odds of long-term success.