Steve Sipress and Daryl Urbanski shared their experiences and insights on building successful businesses, persevering through challenges, and taking action. Steve Sipress discussed their experiences as a vendor at Madison Square Garden and later as an entrepreneur in the fantasy sports industry, emphasizing the importance of understanding the needs and preferences of the target audience. Both Daryl and Steve emphasized the value of experience, resilience, and lifelong learning in overcoming business challenges. They also discussed the significance of crafting an offer tailored to the target market's needs and wants, and positioning oneself on the right side of the cash register.
Here are the reasons why you should listen to the full interview:
- Discover how Sipress transformed various career paths into successful business ventures.
- Learn how to rise above the challenges inherent in starting something anew, such as bankruptcy, and turning them into a stepping stone for success.
- Understand the intrinsic nature of mistakes and how to leverage them as pivotal learning experiences to strengthen your business acumen.
Resources:
- Official website of Steve Sipress
- Follow Him On Social Media Facebook | Linkedin | Pinterest
- Book: Ultimate Entrepreneur Success Secrets by Steve Sipress
- For more Informative Interviews Click Here
Interview Highlights:
Steve Sipress: Entrepreneurship, marketing, and sales with a successful serial entrepreneur
- Steve Sipress is a successful serial entrepreneur and marketer with a long list of accolades.
- Steve's dog, Mr. Old van doggy boy, is no longer crazy or rambunctious but still with him in Arizona.
Entrepreneurship, business, and life lessons
- Daryl Urbanski shared his entrepreneurial journey, starting with collecting bottles and delivering newspapers as a child.
- Daryl Urbanski's father encouraged him to persevere after a poor start with his paper route, emphasizing the importance of resilience in business.
- Steve shares their experience as a paper boy, mentioning how they went from delivering 16 papers to 47, and how they learned valuable skills such as time management and hard work.
- Steve's father was a season ticket holder for the Knicks and Rangers, and Steve got a job as an usher at Madison Square Garden, where they worked for two and a half years.
Job as vendor at concerts, sports games, and events, earning money through hustling and networking
- Steve describes their job as a vendor at Madison Square Garden, where they get to attend events for free and sell merchandise to fans.
- Steve Sipress's job involves working for two hours at each event, traveling to get to the job, and paying for expenses.
- Steve reflects on their past jobs, including pumping gas and serving fast food, and how they prioritized work over leisure activities.
Starting a fantasy basketball league with friends during law school
- Steve started a fantasy basketball league with friends during law school, drafting players and trading them ongoing.
- Steve's game evolved from a one-day pool to a full season league with daily lineups and player trades.
Starting a fantasy sports business in the 1980s
- Steve describes inventing fantasy sports leagues in the 1980s, starting with basketball and later expanding to baseball.
- Steve's friend encourages them to start charging money for their leagues after discovering similar services in an obscure sports magazine.
- Steve Sipress describes their experience working at Madison Square Garden as a high school job, selling peanuts and other snacks to make ends meet.
- Steve's business took off after they started using direct response marketing techniques, despite not knowing much about the industry at the time.
Using toll-free numbers for business and lead generation
- Steve recounts their experiences with telemarketing scams in the mid-80s.
- Steve struggles to convince mother to install toll-free line for business.
The early days of fantasy sports and its growth
- Steve explains how they turned their hobby into a successful business by targeting rabid sports fans with a unique offer.
- Steve's innovative approach, including prize money, helped establish their fantasy sports game company as the largest in the industry.
- Steve Sipress criticizes the idea of giving away prizes as gambling and illegal.
- Steve shares their opinion as a lawyer on the legality of giving away prizes.
- Daryl Urbanski built a fantasy baseball league management system, which he sold for $1.75 million.
- Daryl Urbanski's system automated the process of collecting and analyzing baseball statistics, saving time and effort for participants.
Entrepreneurship, business growth, and burnout
- Entrepreneur regrets not valuing their business accurately, selling too cheaply.
- Steve discusses burnout from creating multiple sports newsletters despite success.
Entrepreneurship, goal-setting, and burnout
- Steve became their biggest client, and the printer would drop other projects for them.
- Steve resented the business due to the ups and downs, and the lack of vacation and enjoyment.
- Steve reflects on past business successes and mistakes, highlighting the importance of inwardly driven goals.
- Lack of goal resetting led to lost drive and motivation, with speaker comparing themselves to others.
The origins and evolution of fantasy sports, with a focus on personal relationships and customer service
- Steve reflects on the origins of fantasy sports, 30 years after starting the first league.
- Steve turned their hobby of sports fanaticism into a business, offering personalized advice to clients.
- Steve Sipress regrets not creating a premium level access league for customers to personally interact with them.
Business struggles and lessons learned
- Steve Sipress describes how a baseball strike in 1990 caused a significant decline in their business, leading to a crash in sales and financial difficulties.
- Steve recounts their struggles to secure loans during the late 80s due to high interest rates and banks' skepticism towards their unique business model.
- Steve Sipress overcame burnout by spotting warning signs and helping others in their business.
Entrepreneurship, business mistakes, and resilience
- Steve ran a successful business for 9 years, then became a consultant
- Steve faced ups and downs, including bad weeks and snowstorms
- Steve shares their experiences of making mistakes and taking risks in business, including getting arrested and selling crack door-to-door.
- Steve believes that their personal experiences make them more effective in leading others, as they have "run out of wrong things to do."
Entrepreneurship, business consulting, and personal growth
- Steve shares their passion for helping others through consulting and problem-solving.
- Steve Sipress discusses their extensive library of books and programs, personalized with handwritten notes and signatures from clients and friends.
- Steve Sipress aims to pass on knowledge and benefits to others through a "name your own price" clearing out process.
Downsizing from a large home to a smaller one, with difficulties in deciding what to keep and what to leave behind
- Daryl Urbanski is downsizing from a large home with a basement to a smaller home without a basement.
- Daryl is struggling to decide what to keep and what to get rid of, despite his wife having already packed the rest of the house.
- Steve struggles with downsizing and parting with possessions, especially family heirlooms.
- Steve and his wife face challenges and delays during a late-night move, including finding a rental truck and navigating heavy traffic.
Leveraging existing knowledge and expertise to create successful products and businesses
- Steve keeps extensive digital collection of notes, sales pages, and products for consulting purposes.
- Steve uses digitized sales letters as an index for digital courses, saving time and confusion.
- New combinations are key, not reinventing the wheel.
- Successful businesses have systems and automation.
- Steve emphasizes importance of being on the right side of the cash register.
- Steve encourages listeners to stop buying and start selling.
- Steve believes that knowledge and expertise can be monetized.
Business lessons from successful entrepreneurs
- Daryl Urbanski and Steve discussed key takeaways from a call, including the importance of having a great offer, target market, and audience.
- Daryl and Steve also emphasized the value of setting goals, building lifelong friendships with customers, and producing content to earn money.
Crafting an irresistible offer for a business
- Steve emphasizes the importance of crafting an irresistible offer from the prospect's point of view, rather than from one's own perspective.
- Steve highlights the difference between selling what people need versus what they want, and how the latter is crucial for success.
- Steve emphasizes importance of giving away free samples to attract customers.
- Offer must be irresistible, but not based on what the business is willing to give.
Business coaching and problem-solving with Steve Cypress
- Steve offers personalized business consulting services through his website Steve Sipress - Founder of The WOW! Strategy™.
- Steve guarantees to help callers immensely on the call and has fun doing it.
- Daryl Urbanski thanks listener for listening and shares invitations for further interaction.
Expertise: Business Growth, Sales, Marketing Automation, Leadership
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