VENTEUR spoke with Daniel Smith, founder of Keepingly, about his entrepreneurial journey. Keepingly is a platform for homeowners to manage, maintain, pay, and keep records of all their home services and expenses. Smith’s experiences drive him as a homeowner focused on empowering homeowners to maintain, manage, and grow their property. He is customer-focused, seeking to create better solutions for stakeholders in the housing industry using data-driven approaches. Smith is a passionate DEI advocate who believes in more equitable solutions. 

The Journey

The entrepreneurial journey is one of self-discovery. What have you learned about yourself while building your business?

I have learned that I have a lot of patience, the will to persevere, and plenty of grit. There are things you cannot control, and business building is a cycle with good, bad, and indifferent moments. Learning to navigate and manage these moments is essential as an entrepreneur.

The entrepreneurial journey is often lonely. Have you experienced loneliness as an entrepreneur? 

Yes, loneliness is built into the experience of being an entrepreneur, especially as a solo founder. 

Sometimes it can be daunting to know the weight of creating the venture is all on your shoulders. One of my most successful strategies has been building a team of people I reach out to and speak with regularly.  This includes everyone from my team at Keepingly to advisors and mentors. 

I delegate tasks to lead and empower my team, allowing them to own decisions around their expertise. Empowering people by giving them room to grow and providing them with a learning space helps build a cohesive unit.

The Psychological Warfare 

Entrepreneurs generally sleep less, work more, and let their health slip. This combination, combined with loneliness, often results in insecurity, self-esteem issues, and low self-worth. Have you experienced any of these issues as an entrepreneur? 

Yes, entrepreneurs personally sacrifice a great deal to take their ventures to the next level. 

While everything mentioned does happen, it's critical to have a community that you can tap into to help validate yourself and what you are building. 

Building a foundation for the business you are starting is necessary. A solid foundation consisting of research and validation was a critical part of my process. 

That process helped me solidify what I wanted to build while consulting experts who provided critical feedback and challenged our thinking. 

Part of the entrepreneurial journey is a mixed bag, so it's essential to ensure that your ego is always in check and be willing to accept feedback. 

Newer entrepreneurs often equate their success with the success and value of their business. If their business fails, they are a failure. If their business succeeds, they are a success. Have you experienced this warped perception of reality? 

No, not at this stage of my entrepreneurial journey. 

If this were the case, on the days that everything goes right and everyone returns my phone call, I would feel like a rockstar and vice versa. 

As a society, we have glamorized entrepreneurship. 

This is especially the case on social media, with influencer culture dominating and everyone thinking that entrepreneurship is all the rage. 

This fuels some of these notions and warped perceptions. 

Being an entrepreneur and then moving to the corporate world, I've built my perspective of success around doing hard work. 

What are your three biggest fears as an entrepreneur, and how do you manage those fears?

My three biggest fears are:

1. Missed opportunities.

2. Fear of the unknown.

3. Letting my team down.

I manage these fears by waking up daily, being thankful for the opportunity to be alive, working toward the objectives for the day, and doing the best I can. 

I control the things within my purview and seek not to let fear cripple me but focus on moving forward and doing the work necessary to build our product. 

The Mistakes

What are three mistakes you made early on as an entrepreneur, what did you learn from them, and how can others avoid these mistakes?

1. A lack of proper partnership agreements.

2. A Lack of proper intellectual property documentation was a mistake I made when I started the business. 

3. Sometimes, success can sour business relationships, so documentation helps protect all parties. Always do your research.  

Daniel Smith, founder of Keepingly

The Successes

What are three seemingly insurmountable obstacles you've faced as an entrepreneur, and how have you overcome them?

1. Acquiring Capital

Funding has been one of the insurmountable challenges that we have faced in building our company. These challenges forced us to focus on being very efficient in our use of capital to ensure we could develop and get our product to market. Market conditions have recently changed, and raising money, which is already challenging as a Black and minority entrepreneur, has challenged us to evolve our strategy. 

2. Attracting Talent 

Finding service providers and fractional services that align with our requirements has been helpful to us thus far, and we plan to continue to use them to be as efficient as possible. 

3. Managing Your Time

Being ultimately responsible for the organization's growth and juggling multiple responsibilities, it is critical to set up schedules that have assisted me in being more efficient in using my time. 

What are three ways you have managed to boost your productivity without causing burnout?

Entrepreneurial life has many masters, and doing everything at once can lead to burnout. Therefore, I try to focus on the following:

1. Prioritizing Tasks

Ruthless prioritization ensures that I can manage to complete and focus on all the things I need to do daily. In the earliest parts of my journey, I tried to answer all masters but quickly realized that I had to make critical decisions. 

2. Taking Preventative Measures 

Proactive management by delegating tasks among team members based on expertise. Aligning internal requirements with weekly goals allowed us as a small team to work better by keeping us on track regarding required things. 

3. Clarifying and Communicating

Communication is a critical element between team members, allowing us to understand what is happening at every stage of our development. This helps to maintain sanity and ensure that the team can remain calm. 

The Advice

How can newer entrepreneurs develop a healthy work-life balance even when it seems like an impossible task?

New entrepreneurs must remember that entrepreneurship is a marathon, not a sprint. There will be good and bad days. Therefore, taking time out and creating routines where you focus on your health by exercising and changing routines by reading and engaging with what is happening outside of your industry provides much-needed balance and clarity. 

What three key pieces of advice would have made your entrepreneurial journey more manageable, and why?

1. Build a Team Including Legal Counsel

Ensure you have a lawyer who understands startups and the process of building a startup. Lawyers who understand startups help navigate seemingly unimportant things but become critical later on, including incorporation, taxes, cap tables, etc.  

2. Plan To Raise Capital

In the tech industry, raising capital is an aspect that is necessary to grow and scale. Therefore, having the plan to present is essential to raising that capital. 

3. Not Every Idea Will Win

Sometimes you think you have a fantastic idea for a feature that will resonate with your market and customers. However, testing will help you validate, and failing fast will ensure you can effectively use resources. 

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