On Asking the Right Questions, Trust, and Flexibility in the Startup World
Hey there, this is Emily from Red Brick. Welcome to our “Mentor Stories” series, where we celebrate and showcase our mentors who are a big part of how we support startups in Red Brick Accelerator. We hope you enjoy reading them!
Mikk Orglaan is an accomplished startup mentor and entrepreneur with over two decades of experience in the tech industry. He has successfully founded, managed, and exited multiple startups and has a proven track record in advising, coaching, and guiding emerging businesses through their early years. Mikk is currently a founding partner and investor in Fstage.vc, a Venture Capital firm registered in Estonia and operating in the pan-Baltic area and Finland.
With his expertise in entrepreneurship, business development, and a few exits of his own, Mikk has become a trusted mentor for many founders, including ours at Red Brick programs. Having a mentor who understands the challenges of entrepreneurship can make a significant difference. Mikk’s understanding of entrepreneurs’ challenges allows him to actively support founders seeking to turn their ideas into successful ventures.
Mikk has extensive experience as an advisor, coach, and mentor, it has equipped him with the skills to adapt his approach based on the individual needs of each entrepreneur. Every startup is different. This flexibility allows Mikk to meet his mentees where they are, whether they need guidance with concrete topics or simply practice sharing their ideas.
Mikk believes that effective mentoring goes beyond simply providing answers; it’s about facilitating the growth of entrepreneurs by helping them discover their own solutions. By asking the right questions, Mikk helps entrepreneurs explore different perspectives, leading them to solutions that they might not have considered otherwise.
“A good mentor is someone who supports growth and asks good questions at the right time.”
This approach emphasizes the importance of not just imparting knowledge but encouraging founders to think critically about their challenges.
Mikk shares a story about a founder who came to him while struggling with an important decision regarding their business model. Mikk realized this founder thrived on independent thinking and creative problem-solving. Instead of delving into technical details, Mikk focused their sessions on strategic thinking and market positioning, which proved to be immensely beneficial for the startup’s growth. Mikk also asked a series of questions about the core values of the startup and the needs of their target market. This guided the founder to reflect deeply on their vision and ultimately led to a breakthrough in their business strategy.
Creating a safe space for open dialogue is a cornerstone of Mikk’s mentoring strategy. He emphasizes the importance of establishing “a circle of trust” where founders feel comfortable to learn without fear of judgment. Mikk believes that the context behind a question often reveals more than the question itself, allowing him to provide insights that are directly relevant to the founder’s specific situation.
Mikk places a high value on the lessons that come from mistakes, both his own and those of the startups he mentors. He shares, “You cannot ask all the questions; you cannot answer all the questions… a good mentor doesn’t rush things.” This shows the importance of patience in the mentoring process. Mikk encourages his mentees to reflect on their setbacks and use them as opportunities for growth.
For example, he often recounts his early days as an entrepreneur when he made several missteps in managing cash flow. Instead of hiding those experiences, he uses them as teaching moments, illustrating how mistakes can lead to valuable insights. He encourages his mentees to adopt a similar mindset:
“It’s okay to fail. What’s important is what you learn from it.”
Mikk’s insights extend to the significance of team dynamics within startups. He notes that “highly competent, highly pragmatic achievers” can sometimes struggle to collaborate effectively. Recognizing this, Mikk is currently exploring how to better assess team dynamics through innovative tools and software. He understands that the relationships among team members can heavily influence a startup’s success.
In one mentoring session, Mikk facilitated a discussion among a startup team that was experiencing conflict. By guiding them to express their perspectives and concerns openly, he helped them identify the root causes of their disagreements. This led to a renewed sense of collaboration and understanding, increasing the team’s effectiveness.
Mikk’s commitment to mentoring Red Brick teams, among many others, is evident and has been active for a few years now. Straightforwardness, asking direct questions, building trust, and encouraging founders to learn from failures are some of the qualities he has as a startup mentor.
As he puts it, “What I consider my responsibility as a mentor is to keep founders off ending up in potholes I have been to. Yet that requires awareness of the context they might not have yet. Sometimes it requires them to share details to build the context, and by doing that we realize in a process what’s actually there to think of.
What I always do while mentoring – is to understand if it makes sense, to all the participants in this business model. How the value is distributed and why would all parties be happy about it. Concept of ICP/ICA is too often yet unknown, together with powerful tools like positioning we usually end up discovering additional or even better income streams.
Annoyingly, founders are often so fond of the idea that they forget that it’s a business. Some claim they are not great at math. Sorry folks, it’s about math from the concept. Validate if it meets ends and returns profits, because it delivers very specific value.”
The bottom line here is that Mikk is a great advisor for helping founders and entrepreneurs confidently tackle the challenges of building scalable businesses. Whether he’s challenging the status quo, pushing founders to build stronger teams, encouraging personal growth, or just being a reliable sounding board, Mikk is the kind of mentor we are delighted to have in the Red Brick network.
Red Brick is thankful for experienced and skilled mentors such as Mikk, who is instrumental in coaching and mentoring our early-stage startup teams. We thank Mikk for his expertise and commitment in helping our teams grow and succeed. 💚Has this inspired you to mentor a startup team? Get in touch, we are always looking for new mentors to join our family!