Mike Cyger: From Fortune 500 to Self-Employment - A Serial Entrepreneur's Journey | Saw.com
Nov 29, 2023
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Mike Cyger, a quintessential serial entrepreneur, discusses his experiences leaving corporate America, selling businesses, organizing conferences with the Department of Defense, positive encounters with the IRS, challenges of getting paid on time, starting a podcast, current projects, and the financial implications of the Voice.com shutdown.
Transitioning from a corporate job to starting a business requires perseverance and the ability to overcome challenges.
Proper financial management, leaving on good terms with partners, and adaptability are crucial in business deals and restructuring.
Domain names play a vital role in establishing online presence and credibility, impacting branding and customer attraction.
Deep dives
Starting a Business After Corporate Life
Michael Siger, a serial entrepreneur, shares his journey of transitioning from a corporate job to starting his own business. Despite facing failure, betrayal, and corporate frustrations, Siger realized he wanted to try his own path. After leaving his corporate job, he started a website called i6sigma.com, which grew rapidly over the years. With the revenue generated from the website, he took a leap of faith and focused on it full-time, leading to further growth. Siger also discusses the importance of leaving on good terms with previous employers and the frustrations of corporate decision-making.
Selling a Business and Buying it Back
Siger shares his experience of selling his business, only to have the deal fall through due to unforeseen circumstances. He then talks about the challenges of restructuring and buying back the distressed assets of his own company. Siger reflects on the lessons learned during this process, including the importance of proper financial management and leaving on good terms with business partners. He highlights the need for adaptability in business and the importance of maintaining trust and communication when navigating challenging situations.
The Importance of Domain Names in Business Branding
As an angel investor, Siger noticed that many startups had poor domain names, which impacted their branding and credibility. This observation led him to explore the domain name industry and ultimately create Domain Sherpa, an online platform for educating entrepreneurs and investors about domain names. He discusses the initial challenges of gaining trust and respect in the domain name industry and how he overcame them by interviewing domain industry leaders and providing valuable content on his website. Siger expresses the significance of domain names in establishing a strong online presence and attracting customers.
Creating Deann Academy and the Value of Training
Siger's experience of training and standardized processes inspired him to create Deann Academy, an online learning platform focused on providing training and resources for sales and business development. He discusses the importance of standardizing training to ensure consistency and effectiveness in sales teams. Siger shares his own experience of using Deann Academy within his business and the positive impact it had on training and knowledge transfer. He emphasizes the importance of continuous improvement and updates in training programs to adapt to the evolving needs of businesses.
The launch and sale of Deann Academy to GoDaddy
The podcast episode discusses the launch and subsequent sale of Deann Academy, an online training program, to GoDaddy. The speaker recalls the initial interest from GoDaddy to purchase the academy and collaborate on marketing efforts. He highlights the integration process and the decision to switch from WordPress to Salesforce. The importance of having UniRegistry as the first corporate customer of Deann Academy is also mentioned, as it provided social proof and helped attract other corporate clients.
The future plans and projects of the speaker
The second part of the podcast episode focuses on the current activities and future projects of the speaker. He mentions the development of a website called insider.email and his exploration of OpenAI for coding. The speaker highlights the potential of AI-generated code and its impact on programming productivity. Additionally, he briefly touches upon the closure of voice.com and shares his perspective on the decision made by the buyer and the challenges faced by startups in the industry.
Join us as we explore the remarkable journey of Mike Cyger, a quintessential serial entrepreneur who took a bold leap into self-employment, leaving behind the security of a Fortune 500 career. Contrary to popular belief, Mike's path to success has been paved with challenges, including the sale of his company not once but twice.
Throughout his journey, Mike has successfully established well-known industry brands like Domain Academy and Domain Sherpa. In this episode, we dive into Mike's experiences, from his leap of faith into self-employment to his investments in his 30s and his ventures in the domain industry.
Mike can be contacted at @MichaelCyger on X.
Timestamps: 0:00 - Introduction 1:00 - The Leap of Faith 7:00 - Investments in His 30s and Lessons Learned 10:00 - Picking Domains and Entering the Domain Industry 13:30 - Internet Publishing: ""The Best Business in the World"" 16:00 - Challenges Faced and Lessons Learned 20:00 - Second Attempt at Entrepreneurship 24:00 - Working with the Government 31:00 - Overcoming Challenges and Learning from Setbacks 39:00 - Selling His Business Again 41:00 - The App Business 44:00 - Establishing Domain Sherpa and Domain Academy 1:00:00 - Domain Name Sales and Uniregistry 1:07:00 - Insider.Email: New Product Launch 1:10:00 - Using AI for Development 1:15:00 - The Acquisition of Voice.com 1:22:00 - Insights from NamesCon
Don't miss this insightful conversation with Mike Cyger about his entrepreneurial journey, domain industry insights, and more.
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About Jeffrey:
Jeffrey M. Gabriel is the founder of Saw.com, a boutique brokerage that specializes in acquiring, selling, and appraising domains. With over 14 years of experience in the domain industry, Jeffrey has a proven track record of closing multimillion-dollar deals and delivering exceptional value to his clients.
Jeffrey's core competencies include remote team management, online marketing, and strategy. He is passionate about helping businesses and individuals achieve their online goals and dreams. He has been involved in some of the most notable domain sales in history, such as Ai.com, Sex.com, and Poker.org. He is also a Guinness World Record holder and a frequent speaker and writer on domain-related topics.
