015: William Caldwell: Life Lessons on Launching a Major App

Meet Will Caldwell, Co-Founder of Dizzle; columnist for Entrepreneur Media and writer for Elite Daily. In this episode, Will candidly and humbly shares his story of being an entrepreneur including lessons learned from his first company ending poorly to his mounting success with Dizzle - an app exclusively designed for real estate professionals and organizations that empowers them to become local experts within their respective communities by creating a trusted network of local vendors and professional services that can be shared with new home owners. Examples include: Insurance Agencies, Plumbers, Contractors, Landscapers, Pool Professionals, Doggie Day Care, Hair Stylists, etc.


Twitter: @dizzle 





Will explains what Dizzle is and especially how he came up with the name. 

Process of building an enterprise level app [09:23]:

Will walks through the genesis of building a large-scale app and explains how he originally intended to start at the individual user level and as he clarity increased on the app's overall usage possibilities, so too did his business. 

Marketing Strategy of Growing Dizzle [10:10]:

Will leveraged his experience as a writer for Entrepreneur Media (Entrepreneur.com) and began building his credibility and outreach through education pieces and writing relevant content for his target audience. 

Insight on Raising Capital [11:39]:

Will expounds upon the importance of networking and explains how he initially raised money through an Angel Investor.  Will emphasizes that an investor will invest more so in an individual than a company, but also to have something tangible to share.

Insight on how to survive as an entrepreneur un the early stages of business [16:12]:

Will wrote an article for Entrepreneur.com that expounded upon leveraging all skills possible to earn an income while starting a business through doing odd jobs at every opportunity as you build your primary business. Will also explains the importance of not relying on one source of income during an initial start-up. 

Big surprise that Will wasn't prepared for [18:30]:

Will explains that his initial product at launch morphed into something much different as his clarity increased for the direct market needs of his app.

Principle Resource for Will [21:59]: 

Perhaps surprisingly - mentors! Will explains his overall positive experience in utilizing mentors in building his company and explains how he was fortunate enough to be coached by the 88th employee at Qualcomm. 

MOOC's Explained [23:04]:

MOOC's or "Massive Online Open Course" are becoming more prevalent with many major universities such as Harvard, Yale, Princeton, etc. and can be accessed by anyone willing to learn.  Will explains how his participation in MOOC's created a networking opportunity to build his app.  Links will be provided below to Will's recommendations. 

Will's biggest challenge [24:04]:

Will stated: if cash flow is king, cash flow is king of the universe!  Will shares that his biggest challenge as a start-up is properly managing his cash flow due to the many necessary, but unexpected expenses that arise. 

How do you view failure as an entrepreneur? [25:14]:

Will's shares that he views failure as "letting down his employees or investors" and shares his experience in his first failed venture as an entrepreneur. He painstakingly walks through that experience and relates the importance of properly setting up contracts in any partnership. 

What has been one of your biggest ah-hah moments? [28:38]:

Will shares how he surprisingly realized that his market for his app was much larger than he initially anticipated and that his clients were willing to pay more for his product than he originally thought.

What is something that you intentionally do every day? [31:56]

Will explains how he loves "unplugging" in the afternoon and goes surfing every opportunity that he gets.

Who inspires you? [32:40]:

Will explains that he is inspired by Elon Musk and several of his investors and his advisors as well as his parents.  He shares how important it is to have support from trusted sources. 

What advice do you have for aspiring entrepreneurs? [34:14]:

Just do it and don't be scared of rejection... You don't know until you've tried and I like to try a lot of things and putting forward the effort. You are not going to build a company unless you put forth the effort. So by just doing it, you are going to learn so much even if you do fail. I can't emphasize that enough. I've tried so many things before we figured this out... Don't give up. Don't get discouraged...

[36:44] Will also explains the importance of learning the needs the people that you want to talk to and really listening to them. 

Recommended Resources

MOOC's or 'Massive Open online course'




For a list of available MOOCs to participate in, visit http://mooc.list.com

Technology Entrepreneurship: This is the course that Will completed

Gorato - Highly recommended by Will. They helped him build his first few apps.


Recommended Books:

Unbroken by Laura Hillenbrand

The Hard Thing about Hard Things by Ben Horowitz

Episode extras

Here are links to several of Will's pieces that he has written for you to check out: