Path to Progress with Paul Heintzman and John Ackerman

Jon Stein, Founder and CEO of Betterment, the country's largest robo-advisor with more than $18 billion in assets under management, shares how he built Betterment and why you should join the future of investing.

Some questions answered in this episode:

• How did you get the idea for Betterment?
• Why did Betterment start in 2008 during the last recession?
• How has Betterment grown so quickly?
• What makes Betterment different and separates it from competitors?
• What is Betterment's company culture?
• What drives Betterment's focus?
• Who are the primary Betterment customers?
• Does it get stressful having so much money under management?
• How has being located in New York helped Betterment grow?
• Why does Jon ride his bike to work?
• What are the biggest highs and lows since founding Betterment?
• What do Jon's days look like right now?
• How often does Jon check email and how does he shut out distractions?
• How does Jon judge Betterment's success?
• Why do so many millennials struggle with long-term saving and how does Betterment help?
• Will Betterment be launching any new products in the near future?
• How many employees currently work at Betterment?
• What advice would you give to an entrepreneur starting out who is hesitant about growing their company?
• What is the best thing you have spent money on in the last six months?
• What additional advice would you give to millennials?

Shoutouts:

• LaCroix
• How I Built This with Jon Stein
• Forbes article with Jon Stein
• Mr. Money Mustache Betterment experiment

Enjoyed this episode? Be sure to open a Betterment account (referral link to get 3 months free). Also, check out our podcast with Keith Blakely to learn more about investing and the economy.

Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.

Rachel Richards, author of Money Honey: A Simple 7-Step Guide for Getting Your FInancial $hit Together, gives us tips on how to write and sell a book.

Some questions answered in this episode:

• Why did you decide to write a book?
• How did you find the time to write?
• What was your background before writing Money Honey?
• What was the hardest part about writing a book?
• What did you learn while writing?
• How did you decide what to cover in Money Honey?
• What outcome did you want from writing Money Honey?
• What advice would you give to someone wanting to write a book?
• How did you promote Money Honey?
• How did you get reviews on Amazon?
• Do you want to write another book?
• What would you change in a revised edition?
• How do you invest your own money?
• What are your tips to retire early?

Last call:

• What advice would your 60 year old self give you today?
  • Work less and have more fun.
• What advice would you give to a recent college graduate?
  • Match your expectations with reality - it will be tough when you first get out f college.
• What is your definition of success?
  • Having a happy family and health.
• What's the best thing you've spent money on in the last six months?
  • Trip to the Grand Canyon.
• What is a book/documentary/podcast you would recommend?
  • The Millionaire Fastlane
  • Rich Dad Poor Dad
  • The Millionaire Next Door
  • The Intelligent Investor
  • I Will Teach You to Be Rich
• What's your favorite thing to drink?
  • Woodford Reserve Double Oaked Bourbon

Shoutouts:

• Weller Special Reserve
• Mr. Money Mustache
• The Penny Hoarder

Enjoyed this episode? Feel free to contact Rachel at [email protected] or on Facebook and Instagram. Also, be sure to get your copy of Money Honey: A Simple 7-Step Guide For Getting Your Financial $hit Together on Amazon. Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.

Alli Truttman, President & CEO of Wicked Sheets, joins us to discuss how she has gone from sewing sheets in her apartment to selling them on qvc.

Some questions answered in this episode:

• How did personal experience form the company?
• How long did you work as a side-hustle before working at Wicked Sheets full-time?
• What did you do to cover your weaknesses operating the company?
• How did you meet your initial investors and make connections to grow your business?
• How do you turn an idea into a product and get it manufactured?
• How long did you sew the sheets yourself?
• How do you get an investor?
• How did having an advisory board help you staff your weaknesses?
• What is the hardest thing you dealt with while starting your business?
• When were you ready to hire an employee?
• Which tasks do you delegate and which do you still perform yourself?
• How do you effectively delegate?
• What has the company been like since it got investors?
• How did you grow Wicked Sheets?
• Why did you decide to switch manufacturers and how did you find a new one?
• How do you amicably part ways with early investors when you need additional investors?
• How do you choose potential investors?
• What are Wicked Sheets and what makes them better than the competition?
• Who would benefit from using Wicked Sheets?
• Did you ever imagine the company/product when you started would look like the company/product today?
• Do you sleep on Wicked Sheets?
• Do you feel like the company has made it?
• What is the difference between your day-to-day now versus when you started?
• What does it mean for the company to be successful and how do you judge success?
• How does taking a break from the company and focusing on other tasks help you see the company from a different angle?
• Is it tough to give up part of your company?
• What is the biggest thing you've learned in the last 10 years running Wicked Sheets?
• What are the best and worst decisions you've made since the company started?
• Why do you need to be able to have a strategy and be able to execute?
• How did you get on QVC and what was the process like?
• Why did you choose to start and run Wicked Sheets in Louisville?
• What is the future of Wicked Sheets?
• Why is feedback from your customers so important for small businesses?

Last call:

• What advice would your 60 year old self give you today?
  • Plan better, faster.
• What advice would you give to an entrepreneur just starting out?
  • Take a lot of risks.
  • Make sure you can pay for health insurance.
  • Stress is normal, you are not alone.
  • Pitfalls will happen.

• What's the best thing you've spent money on in the last six months?
  • One way mirrors on all the doors and windows at Wicked Sheets.
• What is a book/documentary/podcast you would recommend?
  • How I Built This podcast.
  • Sapiens.
  • Shoe Dog.
• What's your favorite thing to drink?
  • Prosecco.

Shoutouts:

• Weller Special Reserve
• Technicolor Pilsner from Bearded Iris
• Upwork
• Bellarmine University
• Costco

Enjoyed this episode? Feel free to contact Alli at [email protected] and make sure to purchase Wicked Sheets at wickedsheets.com, Amazon, or QVC. Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.

Alli Truttman, President & CEO of Wicked Sheets, joins us to discuss how she has gone from sewing sheets in her apartment to selling them on qvc.

Some questions answered in this episode:

• How did personal experience form the company?
• How long did you work as a side-hustle before working at Wicked Sheets full-time?
• What did you do to cover your weaknesses operating the company?
• How did you meet your initial investors and make connections to grow your business?
• How do you turn an idea into a product and get it manufactured?
• How long did you sew the sheets yourself?
• How do you get an investor?
• How did having an advisory board help you staff your weaknesses?
• What is the hardest thing you dealt with while starting your business?
• When were you ready to hire an employee?
• Which tasks do you delegate and which do you still perform yourself?
• How do you effectively delegate?
• What has the company been like since it got investors?
• How did you grow Wicked Sheets?
• Why did you decide to switch manufacturers and how did you find a new one?
• How do you amicably part ways with early investors when you need additional investors?
• How do you choose potential investors?
• What are Wicked Sheets and what makes them better than the competition?
• Who would benefit from using Wicked Sheets?
• Did you ever imagine the company/product when you started would look like the company/product today?
• Do you sleep on Wicked Sheets?
• Do you feel like the company has made it?
• What is the difference between your day-to-day now versus when you started?
• What does it mean for the company to be successful and how do you judge success?
• How does taking a break from the company and focusing on other tasks help you see the company from a different angle?
• Is it tough to give up part of your company?
• What is the biggest thing you've learned in the last 10 years running Wicked Sheets?
• What are the best and worst decisions you've made since the company started?
• Why do you need to be able to have a strategy and be able to execute?
• How did you get on QVC and what was the process like?
• Why did you choose to start and run Wicked Sheets in Louisville?
• What is the future of Wicked Sheets?
• Why is feedback from your customers so important for small businesses?

Last call:

• What advice would your 60 year old self give you today?
  • Plan better, faster.
• What advice would you give to an entrepreneur just starting out?
  • Take a lot of risks.
  • Make sure you can pay for health insurance.
  • Stress is normal, you are not alone.
  • Pitfalls will happen.

• What's the best thing you've spent money on in the last six months?
  • One way mirrors on all the doors and windows at Wicked Sheets.
• What is a book/documentary/podcast you would recommend?
  • How I Built This podcast.
  • Sapiens.
  • Shoe Dog.
• What's your favorite thing to drink?
  • Prosecco.

Shoutouts:

• Weller Special Reserve
• Technicolor Pilsner from Bearded Iris
• Upwork
• Bellarmine University
• Costco

Enjoyed this episode? Feel free to contact Alli at [email protected] and make sure to purchase Wicked Sheets at wickedsheets.com, Amazon, or QVC. Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.

Alli Truttman, President & CEO of Wicked Sheets, joins us to discuss how she has gone from sewing sheets in her apartment to selling them on qvc.

Some questions answered in this episode:

• How did personal experience form the company?
• How long did you work as a side-hustle before working at Wicked Sheets full-time?
• What did you do to cover your weaknesses operating the company?
• How did you meet your initial investors and make connections to grow your business?
• How do you turn an idea into a product and get it manufactured?
• How long did you sew the sheets yourself?
• How do you get an investor?
• How did having an advisory board help you staff your weaknesses?
• What is the hardest thing you dealt with while starting your business?
• When were you ready to hire an employee?
• Which tasks do you delegate and which do you still perform yourself?
• How do you effectively delegate?
• What has the company been like since it got investors?
• How did you grow Wicked Sheets?
• Why did you decide to switch manufacturers and how did you find a new one?
• How do you amicably part ways with early investors when you need additional investors?
• How do you choose potential investors?
• What are Wicked Sheets and what makes them better than the competition?
• Who would benefit from using Wicked Sheets?
• Did you ever imagine the company/product when you started would look like the company/product today?
• Do you sleep on Wicked Sheets?
• Do you feel like the company has made it?
• What is the difference between your day-to-day now versus when you started?
• What does it mean for the company to be successful and how do you judge success?
• How does taking a break from the company and focusing on other tasks help you see the company from a different angle?
• Is it tough to give up part of your company?
• What is the biggest thing you've learned in the last 10 years running Wicked Sheets?
• What are the best and worst decisions you've made since the company started?
• Why do you need to be able to have a strategy and be able to execute?
• How did you get on QVC and what was the process like?
• Why did you choose to start and run Wicked Sheets in Louisville?
• What is the future of Wicked Sheets?
• Why is feedback from your customers so important for small businesses?

Last call:

• What advice would your 60 year old self give you today?
  • Plan better, faster.
• What advice would you give to an entrepreneur just starting out?
  • Take a lot of risks.
  • Make sure you can pay for health insurance.
  • Stress is normal, you are not alone.
  • Pitfalls will happen.

• What's the best thing you've spent money on in the last six months?
  • One way mirrors on all the doors and windows at Wicked Sheets.
• What is a book/documentary/podcast you would recommend?
  • How I Built This podcast.
  • Sapiens.
  • Shoe Dog.
• What's your favorite thing to drink?
  • Prosecco.

Shoutouts:

• Weller Special Reserve
• Technicolor Pilsner from Bearded Iris
• Upwork
• Bellarmine University
• Costco

Enjoyed this episode? Feel free to contact Alli at [email protected] and make sure to purchase Wicked Sheets at wickedsheets.com, Amazon, or QVC. Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.

Maggie Heely, Owner and Lead Coordinator of Weekend Wedding Warrior, gives us tips and tricks to have a great wedding (and a happy marriage)!

Some questions answered in this episode:

• What is a wedding day coordination?
• What is the difference between a wedding day coordinator and a wedding planner?
• Who is a typical client of Weekend Wedding Warrior?
• How far in advance should you book a wedding day coordinator?
• What order should you book venue, photographer, music, and wedding day coordinator?
• How did Maggie become a wedding day coordinator?
• How did Weekend Wedding Warrior's business grow?
• Should you choose your wedding vendors at a bridal show?
• How do you find a good caterer/DJ/photographer if you don't go to a bridal show?
• How many people should you invite?
• What percentage of people you invite to your wedding will RSVP "yes"?
• How long should you be engaged?
• What is the price of an average wedding?
• What are some ways you can save money on your wedding without killing the vibe?
• What do guys and girls care about the most during their weddings?
• What do couples fight about the most during the wedding and after they're married?
• Do you think the length of engagements have gotten shorter or longer?
• What are the secrets to a happy marriage?
• What are the biggest pitfalls during a marriage and what are some tips to overcome them?
• Why should couples plan their own weddings?
• Why should couples hire a wedding day coordinator?

Last call:

• What advice would your 60 year old self give you today?
  • Chill out.
• What advice would you give to an entrepreneur just starting out?
  • Quit your job now and do it.
• What is your definition of success?
  • Getting praised.
• What's the best thing you've spent money on in the last six months?
  • Childcare, vacation to Clearwater Beach, Florida, and Sling TV
• What's your favorite thing to drink?
  • French Roast Organic Cold Brew from Trader Joe's with Almond Milk and Nutpods

Shoutouts:

• Prosecco
• theknot.com
• Adam Padgett Weddings
• Naive
• Rawnaissance
• Gheens Foundation Lodge
• Sweet Surrender

Enjoyed this episode? Feel free to contact Maggie at [email protected] or Weekend Wedding Warrior at [email protected] or call/text at 502-424-4665. Also be sure to connect with Weekend Wedding Warrior on Facebook and Instagram.

Also, check out Part 1 of our Wedding Series with Crushed Ice Catering and The Ice House.

Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.

John Shumate, CEO of Venture First (and the most interesting person we've ever met), teaches us how to take risks and reach our goals.

Some questions answered in this episode:

• Did you see yourself as an entrepreneur growing up?
• How did you make the leap to become an entrepreneur?
• How did you get and keep your first clients?
• What was your day to day like starting out and what where the first few years like running Venture First?
• What is the best marketing tool you have ever used?
• How did you expand Venture First's services from business valuation to outside CFO Services and bookkeeping?
• What does it mean to be a CFO for a company?
• How do you grow your services when you aren't an expert in that service line?
• How do you differentiate yourself in an industry that has a "stodgy" reputation and make finance sexy?
• What separates people who take risks from those who do not?
• How can great things happen from really bad situations?
• What does your day to day look like now that Venture First is more established?
• What are the highs and lows of being an entrepreneur?
• Why does being an entrepreneur suck?
• What are the benefits of being an employee vs. being an entrepreneur?
• Do you think the entrepreneur spirit is genetic or is it something you learn?
• What does Venture First look like today?
• When did you take on investors and how has it changed the company?
• How will you know when you've made it?
• What is the best decision you've made running Venture First?
• What is the future of Venture First?
• Why should people take risks?

Last call:

• What advice would your 60 year old self give you today?
  • Break More Rules, Have More Fun, Work Harder
• What advice would you give to an entrepreneur just starting out?
  • Find a really good mentor
  • Be ready to spend more time and capital than you expect
• What's the best thing you've spent money on in the last six months?
  • Satellite phone (overall best purchase)
  • Nice bottles of bourbon -
• What book/documentary would you recommend?
  • Scaling Up: How a Few Companies Make It...and Why the Rest Don't by Verne Harnish
  • Fight Club (movie or book)
  • The Hard Thing About Hard Things
  • The Advantage
• What's your favorite thing to drink?
  • 1968 Old Fitzgerald
  • Old Fashioned
  • Basil Hayden

Shoutouts:

• Woodford Reserve
• Please & Thank You

Enjoyed this episode? Feel free to contact John at [email protected] and connect with him on Linkedin.

Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.

John Shumate, CEO of Venture First (and the most interesting person we've ever met), teaches us how to take risks and reach our goals.

Some questions answered in this episode:

• Did you see yourself as an entrepreneur growing up?
• How did you make the leap to become an entrepreneur?
• How did you get and keep your first clients?
• What was your day to day like starting out and what where the first few years like running Venture First?
• What is the best marketing tool you have ever used?
• How did you expand Venture First's services from business valuation to outside CFO Services and bookkeeping?
• What does it mean to be a CFO for a company?
• How do you grow your services when you aren't an expert in that service line?
• How do you differentiate yourself in an industry that has a "stodgy" reputation and make finance sexy?
• What separates people who take risks from those who do not?
• How can great things happen from really bad situations?
• What does your day to day look like now that Venture First is more established?
• What are the highs and lows of being an entrepreneur?
• Why does being an entrepreneur suck?
• What are the benefits of being an employee vs. being an entrepreneur?
• Do you think the entrepreneur spirit is genetic or is it something you learn?
• What does Venture First look like today?
• When did you take on investors and how has it changed the company?
• How will you know when you've made it?
• What is the best decision you've made running Venture First?
• What is the future of Venture First?
• Why should people take risks?

Last call:

• What advice would your 60 year old self give you today?
  • Break More Rules, Have More Fun, Work Harder
• What advice would you give to an entrepreneur just starting out?
  • Find a really good mentor
  • Be ready to spend more time and capital than you expect
• What's the best thing you've spent money on in the last six months?
  • Satellite phone (overall best purchase)
  • Nice bottles of bourbon -
• What book/documentary would you recommend?
  • Scaling Up: How a Few Companies Make It...and Why the Rest Don't by Verne Harnish
  • Fight Club (movie or book)
  • The Hard Thing About Hard Things
  • The Advantage
• What's your favorite thing to drink?
  • 1968 Old Fitzgerald
  • Old Fashioned
  • Basil Hayden

Shoutouts:

• Woodford Reserve
• Please & Thank You

Enjoyed this episode? Feel free to contact John at [email protected] and connect with him on Linkedin.

Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.

Erica Outlaw and Lindsay Brough from Crushed Ice Catering and The Ice House teach us how to have a great wedding without blowing our budget.

Some questions answered in this episode:

• How do you transition from the catering industry to the venue industry?
• How do you sell something that does not exist?
• What were the first few years like after opening the business?
• What is the atmosphere at the company today?
• When did the day-to-day job duties transition from 80 hour workweeks to having a team to take some of the load off?
• How do you get millennial employees to buy into the company?
• What are some catering "musts" for your wedding?
• What are tricks to save money on your wedding catering without compromising quality?
• What is a good number of people to invite to your wedding?
• What is the price difference between a buffet and a plated dinner?
• Who is the first person you should talk to when planning your wedding?
• How far in advance should somebody book a wedding venue?
• What does Ice House give you if you visit them to book your wedding?
• Should you hire a wedding planner?
• What are things you can skimp on and what are things you cannot skimp on for your wedding?
• How would you plan the most frugal wedding?
• How much does an average wedding cost?
• Should you have a DJ or a band?
• How do you properly open a bottle of champagne?
• What are tips to save money on a bar without ruining everybody's time at your wedding?
• What is the biggest mistake couples make during the wedding planning process?
• What are attributes of Erica's and Lindsay's favorite couples?
• What are their ideas of a good wedding?
• What advice do they have for somebody getting married?

Last call:

• What advice would your 60 year old self give you today?
  • Slow down and appreciate more.
  • Don't sweat the small stuff.
• What is your definition of success?
  • Providing for employees.
• What's the best thing you've spent money on in the last six months?
  • Trip to the Bahamas
  • Trip to Napa Valley
• What book/documentary would you recommend?
  • Oh Crap, Potty Training
  • Second Life Podcast
  • The Address
• What's your favorite thing to drink?
  • Vodka Tonic with Two Limes
  • Tequila
  • Rosé in the summer

Shoutouts:

• Chandon Sparkling Wine
• Stevie Rays Blues Bar

Enjoyed this episode? Feel free to contact Erica at [email protected] and Lindsay at [email protected]. Also connect with them on Facebook for either The Ice House or Crushed Ice Catering.

Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.

Chip Ridge, President of Millennial Title, teaches us the ins and outs of investment real estate.

Some questions answered in this episode (as always, any views expressed in this episode are personal opinions - do your research and consult a professional before investing in real estate):

• What is title insurance?
• Why did you start Millennial Title?
• What are the different objectives you can achieve with investment real estate (cash flow vs. asset accumulation)?
• Why should somebody invest in real estate?
• What are some of the major factors to consider before investing in real estate?
• Would you rather invest in a commercial, single-family, or multi-family property?
• What mistakes has Chip made while investing in real estate?
• What is the expected time-frame you should expect to hold an investment property?
• Is it hard to find a good real estate deal right now?
• How long does it take to find a good deal?
• Does the current market remind you of the 2007 bubble?
• What is the most important factor in making money in real estate?
• What are characteristics of properties you wouldn't touch?
• What are the biggest benefits of investment real estate?
• Why is leverage so important with investment real estate?
• What are the tax benefits of investment real estate?
• Who should you rely on when you begin investing in real estate?
• Should people manage their own properties or hire a management company?
• What are characteristics of home-run properties?
• How do you sell a company?

Last call:

• What advice would you give to your 22 year old self?
  • Live life in the moment.
• What is your definition of success?
  • Being a mentor and a steward, and being thoughtful every day.
  • Chip is currently undergoing a project called "Block Change" to promote homeownership in communities that traditionally have third party housing.
• What advice would you give to somebody just starting a business?
  • Surround yourself with a strong group.
• What's the best thing you've spent money on in the last six months?
  • His childrens' education.
• What book/documentary would you recommend?
  • Malcolm Gladwell - The Tipping Point
• What's your favorite thing to drink?
  • Sol
  • Lagunitas

Shoutouts:

• Wolf's Ridge Brewing
• Columbus Brewing

Enjoyed this episode? Feel free to connect with Chip on LinkedIn or at [email protected].

Have any topics you want to be covered or amazing people you'd like us to interview? Let us know! You can email us at [email protected]. You can also find us on Facebook, Instagram, Twitter, and Linkedin. Please be sure to subscribe to our weekly mailing list at drunkenmoney.com/subscribe.