Coaching can help startup founders address difficult conversations, establish fair co-founder relationships, distribute equity fairly, and improve communication skills, ultimately leading to team success.

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  00:00

  Startups can benefit from coaching to address difficult conversations and identify root problems, such as unclear roles and responsibilities, which can lead to success or failure.

  • Coaching is a supportive relationship that helps people, usually founders or execs, resolve problems in their work and life, while therapy is a relationship that uses the client's life experience to affect change and requires a longer credentialing process.
  • Startups commonly struggle with having difficult conversations and identifying the root problem, which can be addressed by discussing roles and responsibilities, equity, founder performance, and runway.
  • In the early days of Justin.tv and Twitch, the four co-founders did a bad job at defining their roles and responsibilities, which led to unclear product ownership and frequent disagreements.
  • Debating over minor details without a clear goal in mind can waste time and a coach with laser vision can quickly identify the actual problem.
  • Clear responsibilities led to success in areas such as customer support and website development, while unclear responsibilities caused issues in decision-making for important product features.
  • Debating trivial matters like choosing the color of a bike shed instead of focusing on building it is a common problem, and as Michael's coach, it's important to prioritize and set clear goals.
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  07:27

  Good leadership is about recognizing the most impactful use of skills and building something, not necessarily being disruptive, while recognizing the need to address dysfunction.

  • A team of four founders had their own individual skill sets and responsibilities, including external partnerships and business-related tasks.
  • In the early stages of product development, it can be difficult to recognize the most impactful use of one's skills and to understand that not all skills are needed until all the necessary components are in place.
  • Good leadership doesn't require being disruptive, sometimes you just need to sit there and build something.
  • In the first company, there was a strange dynamic with weird authority roles, while in the second company, there was a natural hierarchy which made it easier for the speaker to delegate tasks.
  • The company had multiple CEOs over time and experienced dysfunction, but eventually recognized the need to address it.
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  12:30

  Resentment towards unequal co-founder relationships can be resolved through self-reflection and renegotiation, while fair co-founder status determination and motivation are crucial for team success.

  • Resentment towards someone who has more than they deserve can cause a breakdown in the relationship, and the solution is to have a self-reflection and consider renegotiating or exploring past reasons for the situation.
  • Identifying patterns that prevent individuals from negotiating for their own self and seeing their own value can affect not only co-founder relationships but also other relationships in their life.
  • Justin set a precedent of treating co-founders as equal partners, which inspired the speaker to fully commit to their online reality TV show, and when Kyle wanted to become an equal co-founder, the speaker had to consider their model for determining co-founder status.
  • Negotiating a deal solely based on individual motivations is not a fair victory as it may not motivate co-founders in the long run, and CEOs should consider the overall effort put in by the team.
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  16:44

  Give employees a lot of equity to keep them in the company, discuss and fairly distribute equity to avoid potential conflicts and ensure mutual satisfaction, and address issues of feeling devalued and lacking confidence in coaching conversations.

  • Equity is like golden handcuffs that keep people in a company, so if you want someone to stay, give them a lot of it.
  • People who feel devalued and hold onto resentment may exhibit passive-aggressive behavior towards the CEO, causing confusion and blindsiding them.
  • Unequal equity can be acceptable in situations where there is a power imbalance, as long as the person with less equity is comfortable with it and there is no risk of future conflict.
  • Discussing and imagining the future of the company with honesty and transparency is crucial for co-founders to avoid potential conflicts and ensure mutual satisfaction.
  • Equity should be fairly distributed and it's important to have open conversations about it, as some people struggle to speak up for their own value.
  • Women and first-time managers often struggle with feeling valued and confident in coaching conversations, which can impact their ability to hold others accountable, and ultimately, it is the CEO's responsibility to address this issue.
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  21:59

  Effective communication is key to success, so find a balance, understand different styles, redirect conversations, and focus on motivation.

  • Over communication is important, but it should be balanced and productive, as too much of anything is not good.
  • Fighting in a team can reduce the value of the company, so it's important to set limits and take breaks to avoid diminishing returns on core goals.
  • Effective communication requires understanding different communication styles and finding a middle ground that works for everyone, separating decision-making from conversation.
  • Redirect conversations about tasks and performance instead of criticizing the person.
  • Performance problems can be categorized as either real or perceived, with real problems being solved through conversation and perceived problems often stemming from unclear roles and responsibilities.
  • Motivation is more important than raw intelligence in achieving high performance, and CEOs should focus on managing motivation to create a positive workplace environment.
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  31:24

  Early stage CEOs struggle to keep their team motivated during the trough of sorrow, which is a skill that few founders possess naturally.

  • Early stage CEOs struggle to keep their team motivated during the trough of sorrow, which is a skill that few founders possess naturally.
  • To stick with a job, it's important to enjoy the work or the people you work with, and have something inherent in the work that anchors you, regardless of success.
  • The speaker discusses the issue of having a short runway in business and how it relates to the fear and stress of not having enough money, which can be a problem for those who need help but cannot afford it.
  • The main problems with runway are not realizing it's a problem, feeling like a failure when it runs out, and the excitement of overcoming it.
  • As a founder, the success of the company depends on your decisions, and getting profitable allows for clear-minded strategic thinking.
  • Socialcam struggled for eight years to find a product market fit and achieve profitability, with the focus on getting a win on the board.
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  38:30

  Coaching can provide valuable insight and support for founders, especially when lacking a community of peers, and learning to have a supportive relationship with oneself is foundational for effective conversations with partners.

  • It's easy to see solutions from an outside perspective, but difficult to gain wisdom and clarity in the midst of chaos.
  • Coaching is helpful because someone who knows you well can provide insight and support, and having a group of people to have coaching conversations with can be beneficial for most founders.
  • Most founders lack a community of peers who are further along than them in their startup journey.
  • Learn to have a supportive relationship with yourself by getting clear about your feelings, goals, schedule, and self-treatment, as it is important foundational work to have effective conversations with partners.
  • To make conversations about responsibilities productive, it's important to step outside of your personal perspective and objectively identify the roles and tasks needed for the company.
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  42:50

  Founders should have collaborative conversations about roles and responsibilities, linking them to company-wide metrics and goals, and be brave enough to have difficult conversations and seek therapy.

  • When having a conversation, focus on the task at hand, use "I" statements, and ask questions to avoid assumptions and effectively communicate.
  • Be explicit and intentional about setting up a meeting with Craig, prepare a script if necessary, redirect his energy towards other projects, and be specific about the date when the podcast will no longer be a part of his responsibilities.
  • When co-founders have a hierarchical relationship, the conversation about ending a failing podcast may be more difficult, but assuming trust and goodwill, it can still be approached as an experiment and discussed openly.
  • Assigning clear roles and responsibilities is crucial to avoid micromanaging and ensure alignment with company goals, while also checking in with colleagues personally to address any concerns or feelings.
  • Founders should have collaborative conversations about roles and responsibilities, linking them to company-wide metrics and goals, and be brave enough to have difficult conversations and seek therapy.
  • Pre-launch is a perfect environment for dysfunction to grow, but the bigger thing is to launch your product, care about the problem, and solve it for the customer.