Finding Your Path Forward After Your First Time Founding A Tech Startup

Microsoft Copilot Generated

Building something by yourself is one of the hardest things you’ll ever do, regardless of your level of success. There are countless guides and tips around how to build your startup. Something not often spoken about is what happens after you build something for the first time. Departing your startup can come in various forms, from becoming acquisition hires, to getting big payouts, to walking away with nothing despite raising millions, or to simply winding down. Regardless of the type of departure, you have gained stories, knowledge, lessons and skills that are invaluable, equipping you with a sense of self awareness and confidence as you navigate the next steps of your journey.

Since winding down my startup, Kleido, I’ve read numerous blogs and reached out to countless former founders for advice. I am sharing with you my observations and lessons I have learned for this next stage, hoping to bring a perspective to consider as you are contemplating departing your own start up (and even if you haven’t yet begun one). Hopefully this perspective illuminates you on a less discussed part of the founder and start up experience.

Microsoft Copilot Generated

As a founder, you often take zero salary while working tirelessly to gain traction or funding. You are taking a tremendous amount of personal, career and financial risk. Often, you might be burning through your own safety nets, especially financially. If you find yourself in a position needing to rebuild while still leveraging your newly earned skills, take the time to grow and reflect on your experiences. Here are some thoughts on how to articulate your story when job searching and find your path forward.

Return to Your Superpowers

Reflect on what you do best and where you’ve become an expert, whether in product, operations, growth, marketing, customer service, sales, coding, or other functions. This may or may not align with your pre-founder experience but should demonstrate progressive responsibilities and learnings. Connect the dots for the recruiter, rebrand yourself functionally on LinkedIn and utilize storytelling to demonstrate to another organization your learnings and gained skills in the process, and how your non-traditional background can contribute to the diversity of the organization.

Switch Your Mindset

You will feel a range of emotions from bittersweetness to disappointment when stepping away from your first company. It’s no wonder people often compare your startup as your child. It takes time to reflect on and express change, learning to acknowledge and process your feelings is pivotal so you can move on. The hardest part is acknowledging and shifting your mindset from being your own boss to working for someone else. Mentally you will need to drop the ego, reevaluate success, readjust your speech and adapt to the role of the interviewee again.

Don’t Forget, You Are Capable

You’ve done whatever it takes to build a company, from figuring out employee benefits to answering customer emails at night. You are a problem solver, fast learner, big picture thinker and you are capable of things outside your expertise. If you enjoy being a generalist and building a business, roles like General Manager or Chief of Staff can offer you a broad skill set while offering autonomy and influence in the direction of the company. Companies hire for expertise and potential, so talk up your function skills, leverage your generalist mindset and speak to your fast learning, cross functional and growing capabilities.

Explore New Industries

Sometimes, you want to zoom out and gain new perspectives in other industries. You might be jaded to the current state and perspective of the industry and want a time out. Identify tangential markets you have experience with, whether through business models, user demographics, or tools you used. You can open yourself to new opportunities, challenge yourself in new industry knowledge and network, and bring a different yet proven approach to the new industry while still contributing functionally or as a generalist.

Let’s Talk Tangible Opportunities

Now that you understand the value you bring and how to tell your story, you might want to consider the following organizations that other former founders have broken through as well as other work environments that either need a scrappy builder and risk taker mindset or are friendly to entrepreneurs.

Microsoft Copilot Generated

1. Join a fast-growing startup: You know the risk of funding, the drill of finding product market fit, and the growing pains of scaling. You can help the startup accelerate even faster as one of the first few employees at a seed stage with a team that respects your building skills and when you can stay objective in decision-making.
2. Spin-offs of larger companies: While rare to find, subsidiaries operating as standalone companies are in need of entrepreneurs to shift the culture. As someone who is used to a fast paced environment, you bring questions, ideas, processes, and tools that challenges the organization to move more efficiently. You can experience fast growth without worrying about the turbulences of an early stage startup and will be secured in funding.
3. Nonprofits tech: If you lean towards impact and are looking for a challenge, nonprofits deploying tools and scaling at startup speed and want to attract more talents who can move faster can be refreshing. The different funder demographics and fundraising model can be interesting to adapt with a focus on donor goals, collaboration and longer term sustainability.
4. Large tech: Google, Facebook etc. have a history of attracting future and former founders. While you can benefit from a stable salary and a good brand name, you might also have to put up with a slower pace of progress and navigate through numerous departments and levels of bureaucracy, but the potential for impact due to the scale of the project and the talents you meet there might just be worth it.
5. In house innovation labs: Switch on your intrapreneurial skills to develop products with all the resources from an established company. You will have to get buy-ins from different departments, pitch for budgets instead of funding, but still have autonomy to innovate that aligns with the company’s overall strategy. Companies might be especially interested in your customer centered approach that understands consumer trends and pain points.
6. Work for an “x” for startup program: AWS for startups, Brex for startups etc… ”x” for startups is a key go-to-market strategy for companies looking to be brought into startups early on or have startups as their main customers, you can support other founders while selling products and services that founders need. You can leverage your background to sell and get great exposure at the founding stages at various industries, it’s a win-win for the companies.
7. Become a consultant: Consulting firms, from large to boutique, offer solutions from various to specialized industries. They are seeking problem solvers such as founders, so that you can practice on solving various problems.

If you are in the position of good financial means or surplus cash after your recent departure, consider these options:

1. Start a new venture: You are probably already thinking about the next startup you want to start, perhaps discovering the problem when building your idea or you want to build another startup with people you liked and worked with. As a second time founder, you will execute faster with a network ready to support you.
2. Start a small business: Whether it is starting a marketing firm or your restaurant, entrepreneurship also comes in different forms and small business can be immensely profitable, just not on a venture level. Introducing technology in markets that is undisrupted but growing can be an exciting challenge. Formats like roll ups and entrepreneurship through acquisitions are getting increasingly popular to get into a new industry.
3. Do your own advising/consulting//fractional support: Enjoy the freedom of being your boss, especially if you have a strong network and an established reputation that refers you to incoming projects.
4. Build your fund: You have seen how hard it is for founders to fundraise and you want to improve the experience for founders like yourself. If you have a theory in finding underrepresented founders or industries through lived experience, consider fundraising from limited partners. You can learn how to build your fund by joining programs like VC Lab.
5. Angel invest: Test your theories on a smaller scale by investing earlier in the process and in founders you believe in.

Some other roles you can consider on a full-time or part-time basis with both financial situations are as follows.

1. Invest at a VC: If you are interested in what it is like on the other side, you can learn how to invest. Despite having a head start as a founder, this path can take years of experience to be good at it. David Teten writes about it at length on his website and articles at TechCrunch on how to break into VC.
2. Scouting roles: As an alternative, you can become a scout for a fund and be the founder’s best advocate. Each fund will have a different deal structure and will be application based or invite only based. Superscout curated a directory of funds with an active scout program.
3. Entrepreneur/Expert-in-Residence (EIR): Most ventures like Khosla host an in-house EIR role to build startups that VCs want to fund or leverage when working with industries they are unfamiliar with. Those roles often have responsibilities to support existing portfolio companies and/or evaluate potential deals.
4. Platform roles: As VCs compete for the founder’s attention, platform roles to support founders in recruiting, operations, community, etc are getting increasingly popular. If you are interested in building more resources and knowledge base for founders, these non investment roles act as a liaison from VC to founders.
5. Venture studios roles: Venture studios validates startups and assembled teams to launch new companies in return for larger equity. If you have a knack for finding product market fit and churning out new ideas, studios like Pioneer Square Labs Labs and Purpose Built Ventures will be a perfect intersection of learning to invest and build.
6. Teach: Students today are curious about entrepreneurship and schools from middle school to community colleges to graduate school are adding courses and electives in design thinking, product development, experiential learning, and venture capital to reflect the demand. Those schools are seeking experienced entrepreneurs to teach the next generation and creating titles like adjunct professors, professors of practice, coaches, or speakers to support teaching.

Here are some tactics that I used and recommend when searching for your next steps.

1. Connect with people who appreciate entrepreneurs: Founders and former founders are most likely to relate, respond to connection requests, and give you a chance. You are likely to hear back from people who mentor entrepreneurs and are involved in the innovation ecosystems. And lastly, people who experienced multiple pivots in functions or industries understood the challenges in navigating new territories.
2. People first, company second, role third: A good idea without a good team goes nowhere, and a good role without funding and a good team can’t achieve much. Focus on finding the right fit with good people where you can enjoy, learn and grow, and have the confidence that that right title will be awarded in time and with the right pivots.
3. Reconnect with past relationships: Leverage your existing network and hit up the power connectors and founders you admired. If you have investors, they are also powerful recruiters. Max Kane wrote about some great templates to connect with past relationships.
4. Hit up the recruiter: Recruiters who are specific to the industries can provide some great insights in how to brand yourself and companies with an entrenpenerial culture. Feargall Kenny has a great article on how recruiters think about candidates with founder experiences.
5. Build your own community: Rather than navigating the next step all by yourself, do it with a community of people you like or an organization with a common mission. Expand your network by building and growing a community that brings you and others opportunities.
6. Write about your experiences: Sharing lessons you’ve learned can help you formulate your personal strategies, help someone in their journey, and draw others to help you.

I hope this article can be helpful as you ponder your next steps. If any of the above resonates or you have resources to add, feel free to reach out to me at abannabao@gmail.com.