On episode 332 of Business Insanity Talk Radio, we answer one of the questions I get asked the most when I travel around the country speaking to small business owners: I know I need to use the cloud, but where do I start? A lot of us are entrepreneurs by accident. You’ll hear one entrepreneur’s unlikely story of how she rose to success. Have you ever seen a cool invention and wished you thought of it? Hear from an entrepreneur who experienced the same thing, then proceeded to make an entire business out of a gag toy. Do you wish you were better at spotting liars? My next guest is a former military interrogator and she’s letting us in on some of her secrets. Finally, who are better professional investors, men or women? My last guest has the answer.

Listen and enjoy:

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Segment 1: Thomas Hansen is the vice president of Microsoft’s Small and Medium Business (SMB) organization worldwide. He is responsible for a team of sales, marketing and partner management professionals to ensure Microsoft’s ecosystem of partners delivers technology-based high value experiences meeting the unique needs of +100 million SMB’s across the world.

1:24 – Most small businesses are sold on moving things to the cloud, but where do they start?

2:25 – What are cloud-based email clients and what advantages do t/hey have?

3:55 – How do you choose a cloud provider?

5:05 – Are cloud services affordable for small businesses?

6:22 – Thomas’s recommendation for moving to the cloud, including risks, rewards and what to prioritize.

7:50 – The advantage of having your own email client.

8:45 – Is Microsoft’s cloud platform agnostic?

Segment 2: Jayna Cooke is the CEO and Partner at EVENTup. As the Vice President of Business Development at Groupon, Jayna was integral in executing the company’s early sales and partnership strategies.  She helped launch various national and local sales strategies and successfully closed the two largest deals to date with national retailers Gap and Nordstrom. She was responsible for creating 25% of entire company revenue in 2009, and 10% of Gross Revenue for 2010.  Jayna has also started her own foundation “Closet Angels” and has invested in several successful Chicago startups including Bucketfeet and Protein Bar.

15:50 – Jayna explains her unlikely path to her current position.

16:42 – The role mentors have played in Jayna’s journey.

18:22 – What special challenges do women entrepreneurs face when starting a company?

19:21 – Sheryl Sandberg says “lean in”, Jayna Cooke says “dive in”.

19:59 – What role does failure play in the growth of an entrepreneur?

21:31 – What is your definition of success?

23:18 – What is “Closet Angels” and what does EVENTup do?

Segment 3: Jonah White is the founder of Billy-Bob Teeth Inc. During a visit to his alma mater, Jonah met sophomore dental student Rich Bailey who was wearing a pair of fake teeth that he mocked up in class. Jonah marveled at the way this simple gag caused peoples’ faces to light up with glee. Jonah knew he had stumbled upon something great and the Billy Bob Teeth Company was born. Jonah is currently hosting ‘Billy Bob’s Gags to Riches’ on the Discovery Channel.

31:33 – How Jonah achieved the American dream, from living paycheck to paycheck to selling over 20 million Billy Bob Teeth.

32:15 – What is the key success factor of Billy Bob Teeth?

34:05 – What was the turning point for Billy Bob Teeth?

35:08 – Jonah discusses what it takes to be a successful inventor.

Segment 4: Lena Sisco is a former military interrogator at Guantanamo Bay. She has interrogated numerous detained members of Al Qaeda and the Taliban. She taught these skills to defense department personnel for years afterwards and now has a new book out that is called You’re Lying: Secrets from an Expert Military Interrogator to Spot the Lies and Get the Truth.

40:45 – What was it like being a female interrogator at Guantanamo Bay?

41:23 – In everyday life, why do people lie?

41:52 – What are the three types of lies and two types of liars?

43:18 – What are the signs of everyday liars?

44:29 – How can people in business extract the truth?

45:15 – If you suspect someone is lying, ask this question.

45:35 – If you catch someone lying, what should you do?

Segment 5: Meredith Jones is an internationally recognized researcher, writer, speaker, and expert in the alternative investment industry.  She is best known for creating industry-leading hedge fund research.

49:31 – Who are better investors, men or women?

50:05 – How do men and women’s investment strategies differ?

50:46 – Why we should broaden our definition of diversification to include investment behavior in addition to strategy and assets.

51:35 – How will having more women at the top of the investment world will benefit us all?

52:15 – If a woman wants to get ahead in the field, what does she have to do?

Sponsored by Sage and Nextiva.