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Lessons from the Long Road: A Founder's Twenty-Year Trek (Part II)

Read Part II of an inspiring journey as Gaby navigates innovation and venture capital in the legal tech landscape

In my previous post, I shared how my over twenty-year journey started, capturing the essence of our vision to stay ahead of innovation and our commitment to execution. As I reflect on this extensive period, filled with myriad business experiences and life lessons, I feel compelled to distill some of the most significant insights I've gathered along the way.

Business

#1. Begin with a vision. Your products and services may evolve, but a strong vision remains your guiding star, always pointing you in the right direction. This clarity helped us navigate the complexities of building and growing a business.

#2. Revenue is not the goal; it's an outcome. It might sound cliché, but revenue is an exchange for value. If you offer something that solves real problems, customers will pay for it. The real aim is value creation. Focus on adding value, and revenue naturally follows. This simple yet powerful truth reshaped our approach to business.

#3. Bootstrapping is hard. Starting your own business is grueling, but bootstrapping is even harder. It demands immense discipline and allows us to control our destiny. For our type of business back in the day, I believe we made the right decision. However, if I had to do it all over today, I might reconsider.

#4. You can build a successful tech company with your spouse. Against conventional wisdom, Dani and I embarked on not just one but two successful tech ventures together. Contrary to some advice, working with your spouse can be a superpower if managed with care and respect.

#5. Beware of the advice trap. As Vinod Khosla aptly put it, deciding whose advice to trust is one of the hardest decisions for a founder. We learned to value advice from those who truly understood our industry's challenges and intricacies. Discernment is key.

#6. Embracing the power of “NO”. Learning how and when to say no was transformative. “No” isn’t negative; it pushes us to develop better arguments and be more creative. You can't be all things to all people. Dani, our “Mr. No,” helped us stay focused and true to our mission. Saying no maintained our clarity, prioritized our efforts, and ensured our product resonated with our Ideal Customer Profile.

#7. The hidden virtue of listening. We've often been led to think that the person who talks the most knows the most. It's natural to want to show our customers and employees that we know what we're doing. But remember, every time we talk, we miss a chance to learn something new. In business, there's pressure to have all the answers, but the real magic happens when we stay quiet, understand the problem, and ask thoughtful questions. If you're talking more than listening, it might be time to make a change.

Execution

#8. “Vision without execution is hallucination” - Thomas Edison. I've echoed the sentiment that “there's no such thing as a billion-dollar idea—only a billion-dollar execution.” At the end of the day, execution is all that matters, and without the right team, guidance, playbooks, and frameworks, it’s incredibly hard to continue to grow and scale.

#9. Frameworks for decision-making are crucial. Another cornerstone of our success was the establishment of solid decision-making frameworks. These frameworks became our playbook, helping us avoid costly do-overs and streamline our processes, proving indispensable over time.

#10. Technical excellence. Building the best technology in the market was another non-negotiable for us. In the tech industry, falling into technical debt can significantly hinder your ability to market effectively, compete, and deliver an outstanding customer experience. Our stellar tech team was pivotal in maintaining our technical edge.

#11. If you build it, they will come. It is nothing further from the truth. You can have an amazing product and the best tech; however, understanding your market segment, mastering customer acquisition, and strategically bringing your product to market are what moves the needle.

#12. Obsess over messaging and keep it evolving. Your messaging defines you and your company. Whether pitching to investors, selling to customers, building marketing campaigns, or hiring employees. You need to perfect it, simplify it, and let it evolve to stay relevant and resonate with your audience. “The best messaging is both hard to find - and obvious once found.” - Alex James.

#13. Resist the temptation of shiny objects. When building a product, everyone—prospects, clients—has an opinion or a new feature that seems essential. It's easy to think you'll lose a customer or revenue if you miss that. However, it's crucial to understand your Ideal Customer Profile (ICP) and stay true to your vision. More features mean more problems. Stay focused and keep moving towards your goals.

#14. Get outside your comfort zone, often. As a founder, you need to be good at many things. I had to push myself to do things I didn’t think were possible or suited for me. I loved product and operations but was afraid of sales. Getting out there, learning, trying, failing, and later seeing the results and actually excelling is incredibly rewarding. As a non-native English speaker, I continue to be out there … working on developing my public speaking skills.

Leadership

#15. Diversity is a force multiplier. As a founder, the last thing you want is to be stuck in an echo chamber. Embracing both cognitive and demographic diversity exposes your company to different perspectives and backgrounds, challenges the status quo, and leads to more creative solutions. Diversity attracts more diversity, so be intentional about that.

#16. Culture radiates from the top. Early on, we made it a point to codify our company culture and integrate it into every facet of our organization. This not only made us accountable but also ensured that everyone on our team could thrive within and embody these values.

#17. Always be curious, always ask questions. A relentless curiosity and a passion for learning have been at the heart of my personal and professional growth. From daily interactions with customers, employees, and vendors to life lessons from my two wonderful sons, every day offers new opportunities to learn and expand my horizons.

#18. The work-life balance dilemma. As a female founder, CEO, mother of two, and wife, that was one of the most common questions I was asked: “How do you manage it all?” And for those waiting for the perfect answer to that question… there is none. And that’s because you are the only one who can define what work-life balance is for you, not a book or motivational speaker. For me, it was living a full life with the fewest regrets.

#19. Lead with empathy. As Maya Angelou wisely said, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.” Being genuine and showing empathy fosters trust and strengthens relationships within teams. In business, people buy from people. Your company is more than a product; it's the trust others place in you. Live up to that.

#20. You define your retirement. As I approach what many call 'retirement,' I find the term a misnomer. I lost count of the “congratulations” said in a tone of condolence when I said I was retiring after my second exit. And then I would hear, “I could never do that; I need something to do.” Retirement isn't about ceasing to do things; it's about achieving the freedom to pursue passions on my terms and achieving economic independence, a topic I'm eager to discuss in a future post.

Building a startup is indeed a long game. It involves delays in gratification, constant trade-offs, and numerous sacrifices. But each day, as we strive to positively impact our customers and push towards our goals, the effort feels worthwhile.

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