How can you document and reflect on your startup journey?

In my experience, the best approach is continuous documentation using the tool that's easiest and most accessible. For most founders, that's their email. Recently tho, my co-founder and I started trying a new approach that leverages AI and LLMs in addition to emails. Here is how it works: 1. We both email each other a daily summarized updates, thoughts, notes, comments, and so forth. All in just one message at the end of the day. 2. Weekly or monthly, we process these emails using LLMs and create a summary. Overtime this starts to shape the story together including both perspectives.

To effectively document and reflect on your startup journey, a structured yet simple approach can be helpful. One method is to send daily email summaries, capturing updates, insights, and challenges. These emails can then be processed weekly or monthly using AI tools to generate comprehensive summaries, offering a clear view of progress and lessons learned. This method allows founders to track both personal and business growth, identify patterns, and refine strategies over time while maintaining a cohesive narrative of the startup's development.

To me, there is only one format that makes sense - build your startup in public, documenting your journey across socials as soon as possible. It's free marketing and user research. Content also brings new followers, making it easier to build brand awareness, hire and generate new leads. So instead of documenting in private, share your learnings across socials whenever they happen.

Actually writing down the journey is something as a founder I have been poor at. But the journey has been documented through interviews, podcasts, articles and even LinkedIn Posts. I would advocate being very active in telling your story and that shall ensure you can look back through multiple formats and reflect on how you were doing at that particular time. Telling your story via various media outlets also forces you to focus, do your research and be concise and engaging. So hopefully, when you look back, the story shall be something you will want to read and reflect on.

As entrepreneurs, it is human to tend to oversell our startup story and convert it into a personal success tale. In my opinion this is wrong. I firmly believe that it is the responsibility of all entrepreneurs not to contribute to idealizing this path, which on many occasions the story of the startup is retrospectively told as a fable of success. Entrepreneurship is a much harder path than is usually thought, in which luck is a decisive factor and which is not for everyone. That is why a large part of the startup's storytelling must be dedicated to talking about the sacrifices, failures and corpses left along the way so that readers can decide more discerningly if it is really worth it for them.

The beauty of documenting your journey on socials is that you can reap several benefits (free marketing, feedback, user research, leads) -regardless- of your main purpose for documenting. Since most weeks will be so busy, writing down learnings and mistakes is probably the best long-term purpose. But note that if you write well, and consistently share valuable content, it may become a key marketing pillar for your business. Most people publish quick low-effort thoughts, and get quick low-quality results. Don't!

Clearly articulate the purpose of your documentation. Are you aiming to track progress, share lessons learned, inspire others, or attract potential investors? Use AI to analyze your goals and tailor your content accordingly. Engaging with your LinkedIn network can help refine your purpose based on community feedback and expectations. Defining your purpose gives direction to your documentation efforts, ensuring that your content remains focused and impactful.

Clearly outline why you are documenting your startup journey. Is it to track your progress, share your story with others, seek advice, or reflect on your learnings? Having a defined purpose will guide your documentation process and keep you focused. It will also help you determine what kind of content to include, whether it’s daily updates, lessons learned, challenges faced, or milestones achieved. A clear purpose ensures your documentation remains relevant and useful both to you and to your audience.

In any field, the process of learning is best undertaken by knowing what you want to learn. This is no less true in the field of entrepreneurship. By focusing your attention on a single aspect of the venture, the potency of the learning process is magnified. Your attention is fixed on that area of the venture, and you'll find lessons everywhere. Use your journal or dossier to capture those lessons just as a scientist conducting a study. Venture With Vision 😎

Authenticity, honesty and your broader tone of voice will vary according to the personality of each founder. If you follow my advice and document your journey on socials, experiment until you find a style that suits you personally, so you actually enjoy doing it. Mistakes and learnings often get good engagement because most people want to play it safe and post to look good. So, document your learnings accurately whatever they are, and allow others to learn from you along the way - you'll continue to build a reputation as someone interesting others can learn from.

Share your experiences authentically and honestly, including both successes and challenges. Use AI-driven sentiment analysis to gauge the emotional tone of your entries and ensure they reflect your true experiences. Authenticity resonates with your audience and builds trust. Engaging with the LinkedIn community can provide support and encouragement, fostering a genuine connection with your followers. Being honest in your documentation helps others relate to your journey and learn from your experiences.

Building trust with your audience requires you to be true and honest when documenting your startup's story. Consider a founder who discusses the highs and lows of their entrepreneurial career, such as the difficulties of obtaining capital and the thrill of product releases. By being open about their experiences, the founder builds trust and authenticity, which resonates with their target audience. This strategy not only humanizes the company, but also generates a sense of connection and empathy, resulting in a devoted following.

Be realistic - the more real the data/documentation is, the better. What have you actually done or achieved? This is supposed to be a helpful tool so do not make it worthless by approaching it with bias, exaggeration, sugarcoating or delusion. Prepare to be uncomfortable.

No hagas "storytelling" de éxito vacío. La autenticidad vende más que cualquier éxito ficticio. Comparte tus aciertos, pero también tus fracasos, dudas y momentos oscuros. La gente se conecta más con las historias reales, no con el postureo. No es un diario de quejas ni un currículo inflado: es tu historia tal cual. Agradece a tu equipo y sé sincero sobre los desacuerdos, pero sin filtrar tu IP. La transparencia cautiva, pero la honestidad brutal engancha.

Another strength about documenting on socials is that feedback is super fast. Look at the comment section and your overall engagement - if nobody cares, you probably need higher quality content. Which means better insights, or better copy-writing.

Define a goal, plan the move and execute the plan and review the result. These three simple steps are enough, nothing less or more

You can get feedback directly from your team, advisors or peer group before you post. You can review the data on posts, blogs or newsletters to check the level of engagement you've had. You can also check the comments to get a sense of how relatable your posts are and how engaged people are with it.

Solicit feedback and input from peers, mentors, and your LinkedIn network. Use AI tools to gather and analyze feedback efficiently. Encouraging others to share their perspectives can provide valuable insights and improve your documentation process. Engaging with the LinkedIn community allows you to gain diverse viewpoints and enhance your content. Asking for feedback helps you grow, adapt, and ensure your documentation remains relevant and engaging.

Involve your team, mentors, and peers in the reflection process. Their perspectives can provide valuable insights, highlight blind spots, and enrich your understanding of the journey. Engaging with your community fosters a sense of shared experience.

The best way I've found to do this is by sharing spontaneously on socials when something important happens. If you have to block time to force yourself to document events, it's much easier to lose motivation and think "there are more important things to do right now". Event -> learning -> share it -> done. Your post history will be the full product.

Regularly revisiting and updating your reflections helps track your evolution over time. It's an opportunity to see how obstacles were overcome, how far you've progressed, and to recalibrate your goals and strategies as needed.

Documentar tu viaje no es un álbum de recuerdos estáticos. Es un proceso vivo que debe evolucionar contigo y tu startup. Revisa y actualiza tu contenido regularmente para mantenerlo relevante y realista. Elimina lo obsoleto y resalta tus nuevos aprendizajes y logros. Mostrar tu evolución no solo demuestra transparencia, sino también tu capacidad de adaptación y crecimiento. ¿De qué sirve tener un diario si nunca vuelves a leerlo y aprender de él?

Regularly review and update your documentation to reflect new insights, progress, and changes in your startup journey. Use AI to analyze patterns and identify areas for improvement. Consistent updates keep your content fresh and relevant. Sharing updates on LinkedIn can maintain engagement and demonstrate your ongoing commitment to transparency and growth. Reviewing and updating your documentation ensures it remains accurate and valuable over time.

Regularly review and update your startup journey documentation. It's an ongoing process to track progress, reflect on changes, and capture learnings. Update to reflect current challenges, opportunities, and growth. Archive or remove outdated content to maintain relevance and clarity.

It is easy to document what, when, where and who. Make sure to ask yourself "How" and especially "Why" and document the answers.

Leverage your documentation as a tool for reflection, learning, and growth. Use AI to identify trends, successes, and areas needing improvement. Reflect on your experiences to make informed decisions and refine your strategies. Sharing your reflections on LinkedIn can inspire and educate others while reinforcing your personal and professional brand. Using your documentation as a tool enhances its practical value and contributes to your overall development.

Documenting your journey in this way, whether it's through LinkedIn posts, newsletters or blog posts, can take time and effort, but it's not the end; it's a useful tool for reflecting on your wins, losses, mistakes and lessons learnt. You can use it to foster introspection and to help guide future decisions and actions. It's a great way to teach and inspire other founders on the same journey and help them develop a roadmap that uses some of your experience or learnings.

Casey Neistat is a perfect example of documenting the journey, leveraging YouTube for the launch of BeMe, which was later acquired by CNN for $30M. Your documented journey can be a powerful tool for introspection, learning, and guiding future decisions. It can also serve as a roadmap for others following a similar path, offering valuable lessons and inspiration derived from your experience.

Your documentation is an effective tool for optimizing your startup experience. Use it to make informed decisions and establish specific goals. Communicate your vision and value proposition clearly. Celebrate accomplishments, learn from disappointments, and adapt to change. Your documentation should inspire you, your team, and your target audience. It's more than simply a record of your experience; it's a roadmap for navigating the challenges and opportunities of startup life.

Securing investment with the wrong co-founders startup. This partnership is like a marriage, but it lasts longer. Launching a venture with individuals who don't align with your vision, work ethics, or expectations can not only stunt the growth of your business but can also breed conflict and toxicity. So, before taking the plunge and accepting investment, it's critical to assess the compatibility and commitment level of your co-founders. If you foresee issues down the line, it takes more courage to abort mission than to sail into a storm. Remember, the journey of entrepreneurship is a marathon, not a sprint. If the foundation isn't robust, having the fortitude to pull the plug early can save years of struggle and potential failure.

Documenting and reflecting on your startup journey is crucial for learning and growth. Keep a detailed journal, capturing key milestones, challenges, and lessons learned. Regularly review and analyze this documentation, identifying patterns, successes, and areas for improvement. Use it to inform future decision-making and inspire continuous innovation.

If you have clear milestones and metrics, these can be anchoring points for you to check in with. This can be quantitative data which could even fit in a ppt or spreadsheet, but you also need qualitative data - seek feedback from customers, partners and investors. You should also take some time to self-reflect. Check in with yourself. If you can pull out soundbites or themes from this qualitative data, you have other insights and forms of feedback to help you understand your journey. Only when you have that self-awareness can the whole picture be clear and ready for a reaction! A startup is a legal person, as are you. Both need to practice awareness and find the right "therapist" in order to understand the past, present and future.

Two things that I have found useful... 1. A good visiting/business card 2. What I call "drawing room marketing"... getting people together over a cup of tea or a meal at home Both sound old-fashioned, but they work!!

Keep writing all your experiments and their results either in public or only with your team. Consider regular retrospectives.