Plan Your Start Podcast

How do you go from growing up so poor there was sometimes no power or food in your home, to self-made millionaire in your twenties, to losing it all and then climbing back to build a product that now ranks as one of the top 6,000 websites in the world? Well that’s the rise, fall, and then rise story of RJ Garbowicz. Hear how he built a Social CRM platform that just crossed over 6M members and has a business model that gives 50% of revenues back to the users - hundreds of thousands of dollars paid out already. Now he’s pretty sure he can create 1 million millionaires on the platform.   SPONSOR: SecureStartup (https://securestartup.com) - Securely and efficiently manage all of the documents between founders and investors.   Opening: Allen and RJ discuss how long Allen has been following RJ’s platform webtalk and the exponential growth over the past few years, despite Goliath competitors in the space.   1:34 RJ explains his journey of getting webtalk to 6 million users and his 600k personal followers.   3:30 Allen talks about the comparison to LinkedIn and other social media platforms and RJ explains how webtalk takes those concepts much further (i.e. how about some basic CRM and contact management functionality); and rewards users for engagement.   5:00 RJ breaks down LinkedIn’s approach and business model and where that platform falls short.   9:20 Allen talks about a key incentive to using webtalk, the “sharing the pie” model.   10:20 How webtalk created massive growth utilizing a reward and revenue sharing system for engagement.   16:10 What is RJ’s message to entrepreneurs? It’s a long, hard road.   17:10 Opening Question: How determined and deranged must an entrepreneur be for success? What is the entrepreneur disease?   18:05 RJ says that entrepreneurs sometimes reach the end of their journey when they are too exhausted and need to exit. The bigger your goal, the more difficult. “How bad do you want it?”   19:25 RJ lists a plethora of negatives to being a startup founder when seeking different levels of success. Allen and RJ discuss how your decision to strive for achievement can affect your social life and those around you.   23:17 RJ talks about his history with entrepreneurship and when he knew he was an entrepreneur - it started in grade school!   24:42 Allen and RJ discuss the obsession that is making money while RJ talks about his struggle as a child growing up with very little.   26:00 RJ talks about his first established business in high school. He started a lawn care service through which he hired a couple of his friends to work for him.   26:40 The problems he experienced by being young and having expendable cash, were lots of dangerous vices. He attended military school shortly thereafter to help get his life back on track.   29:10 RJ lost his privileges to drive before he was even old enough to drive because he bought a car for cash at the age of 15!   30:20 Allen lists all of the jobs RJ worked over the years, and RJ learned he could do everything that the companies did and make more money. He harnessed his entrepreneurial spirit and grew ANOTHER business.   33:15 Allen referred to his previous interview with Steve MacDonald, and how some owners sell out too early and short-change both themselves and their investors. His suggestion is to strongly consider hanging on a little bit longer.   34:20 RJ took his check for selling his company and some time away in order to figure out what his next steps were. He learned through years of entrepreneurship, that the Internet and tech was the way of the future.   35:35 Started an online real estate business in 2005, where he was met with rapid growth but short lived success.   37:20 RJ tells how he survived his loss. “Do what you gotta do. I grew up so poor all I had to eat some days were condiments. I can survive this.”   39:10 RJ says “Once you realize you can survive with nothing. You are willing to bet everything”   41:00 He learned early to go after high cash-flow jobs to earn his capital to get some skin back in the entrepreneurship game even after a loss.   41:30 Allen questions RJ about when he created his local nightlife-to-Internet business, and how he monetized the platform.   42:52 The dangers you face when taking on investors (you can be kicked out of your own company) and how RJ navigated his negative experience.   46:20 The birth of webtalk. RJ explains how he came up with the concept, and what problem he wanted to solve for his lifelong journey.   54:10 Allen goes through a guided walkthrough of some of the services of webtalk with RJ.   59:54 RJ gives a brief overview of the roadmap for webtalk throughout the next year - including launch of the mobile app.   1:02:50 Allen asks RJ the final question: “Where do you see yourself in 5 years?”   Webtalk: https://www.webtalk.co   Plan Your Start: https://www.planyourstart.com          

In these challenging times, we need to hear from entrepreneurs like Christina Dills. After rapidly rising the ranks at Microsoft from intern to Channel Development Manager for all Latin America. Christina was a rising corporate star - but something was missing. She felt unfulfilled and that there had to be more to life, contribution, and work. So she began her research, made a plan, and Quit to Start. Hear how she did it and how she now prioritizes the mind and spirit in her daily routine as a startup founder with intention, gratitude, and exercise - resisting negative thoughts and negative energy. A daily work and life strategy to strongly consider in these times - and all times. SPONSOR: SecureStartup (https://securestartup.com) - Securely and efficiently manage all of the documents between founders and investors. Opening: “Life is Beautiful” written on the office wall behind Christina. She explains her belief that words have energy. 1:47 Discussion on gratitude and how it is the best cure for negative thoughts. Christina explains how energy frequency ties into living at your best. 3:45 Setting your intentions and how to manifest them. The best way to to predict your future is to create it through your thoughts and your intentions every single day. 7:20 Christina gives her recommendations to early entrepreneurs: always set up your day with intention, gratitude, and exercise. 9:00 Allen saw Christina recently pitch her startup. He asks her about the experience and she talks about why pitching is part of the journey and it's good for you. 14:55 Cristina explains how she became less and less fulfilled at her job and why she had to plan her escape. 18:00 Despite the amazing lifestyle and personal finances of her corporate job, she felt that she was missing something bigger in life. 21:28 Christina discusses how she self-funded her startup and then discussion on the downsides of taking investment. 26:40 Believe in yourself, who knows your business better than you? Whose two cents matter to you as a founder? The mentality of others cannot affect your vision. 31:40 Allen explains one concept in his book “you are a threat” and Christina talks about the lesson she learned from telling others about her potential start. Who can you trust? Who can you talk to? 36:50 Keep it quiet until you get momentum. 37:50 Finding the people that compliment you and you can trust. 40:20 Allen talks about confidence and the mindset behind its perception both inside and out. 42:08 Growth in business is the same as growth through exercise. Sometimes it’s painful, but you have to push through in order to grow. 43:30 Christina walks through her childhood and high school years, and the most valuable lesson she ever learned, her grandmother taught her - “education is your ticket”. 49:00 Christina explains that she has always had the entrepreneurial spirit and was always experimenting with startups on the side. 52:00 Your entrepreneurial journey is whatever you want it to be. You don't just magically become an entrepreneur, you grow into it. 54:00 Rising the ranks at Microsoft - she explains her unrelenting drive to learn. 57:00 Christina talks about the stress of life and how to heal yourself in a stressful environment. 1:02:00 Allen and Christina discuss the risks of entrepreneurship and how we weigh it against risk of not making the change or not taking action. 1:05:15 Allen talks about the hidden aloneness and anxiety of entrepreneurship - Christina talks about how she persevered through it. 1:06:40 Taking the leap. Christina talks about the moment she knew she was going to leave and start her company. 1:13:40 Discussion on facing your fears and gaining the escape velocity needed to become an entrepreneur. 1:15:16 Christina discusses detaching the tentacles of the workplace and the removal of comfort to embrace your future. 1:18:00 Christina talks about getting into the abundance mindset. The belief that good things are going to happen and avoiding the negativity of the scarcity mindset. 1:22:10 Think about getting somewhere and do it on purpose. Christina explains that “you can choose your thoughts like you can choose your clothes”. 1:23:20 Christina explains the value of starting broad and intentional in your thoughts and then moving to specificity. 1:25:00 Final thoughts - be open to the flow of the universe and believe in yourself and don’t let others deter you. Smart Edge Technologies: https://smartedgetech.io/ Plan Your Start: https://planyourstart.com

How does one come back from an epic two decade run of entrepreneurial success - then to watch it slowly evaporate around you as market forces shift? This is the story of Brad Kugler and the building of an eight figure cash flowing business that brought him and his family the life and freedoms every entrepreneur dreams - then the crash, the fight for survival, and the epic comeback. Brad tells his rise-fall-rise story, how he learned more on the way down than on the way up, and how he’s now growing again in triple digits for 3 straight years - and disrupting an $8 billion dollar market. SPONSOR: SecureStartup (https://securestartup.com) - Securely and efficiently manage all of the deal documents between founders and investors. Opening: Allen and Brad talk about how they first met almost 20 years ago when Allen helped Brad create his first e-commerce website & order management platform. 4:10 Brad talks about how his big run started - taking over his dad’s VHS movie media distribution business. It had revenues of $2M with about 10-15 employees - by 2012 Brad had grown it to $25M and about 55 employees. 7:30 Allen and Brad talk about how what he's doing now with direct mail has parallels to what happened to him with the movie media distribution business - but this time he is the disruptor. 9:10 How does Brad's current business Direct Mail 2.0 work? Direct physical marketing mail traditionally has a very low response rate. With Direct Mail 2.0's technology, companies typically see a dramatic 25% to 50% increase in response rates - and with tracking capability they've never had before. 16:40 Brad talks about growing up in the Chicago area and how his great grandfather, an immigrant, started a window cleaning company that expanded to janitorial services over three generations, to his grandfather, and then to his father. 19:10 Brad’s father purchased a movie VHS media distribution business in Florida and by the early nineties, Brad took over the helm. The business did very well for the next 15+ years and Brad, with his brothers, were able to buy out dad. 25:10 He tells the story of when DVDs arrived - Wizard of Oz was the very first movie on DVD. Brad sold 30 copies in 30 seconds on eBay, that was his clear sign to transition to DVD from VHS. 26:25 Brad and his company achieved #1 DVD seller status on Amazon for several years. Brad once had a meeting at Amazon headquarters and Jeff Bezos walked in - one of many meetings to come with Jeff Bezos. 34:05 Allen asks Brad about what it was like making so much money in his thirties - and the incredible personal freedom, toys, and opportunities that came with the success. 41:30 Then a storm started brewing - a flat year in 2012, the first in a decade. Then in 2013 things got worse - the advent of online movie streaming had begun. The business began to free-fall over the next few years, unable to pivot fast enough. 48:25 Brad says he learned way more going down than going up - how to stretch cash flow, navigate legal, problem solve, etc. The company was forced into bankruptcy - but he was able to buy it back on the courthouse steps as a tiny shadow of its former self. 51:30 He stayed determined - he learned bootstrapping at the end of success, not the beginning like normal. He became profitable albeit small, never missed a payroll, never bounced a check. 53:10 The company limped along until he got a call one day from an ex-employee, top salesperson from 20 years prior. Her name was Joy and she now had her own massively successful direct mail print marketing company. 54:55 Joy said she had watched how Brad had fought and persisted in the business despite adversity - she was impressed and offered him to take over a direct mail software technology product she had developed in-house. 57:10 Being in-house with the larger company helped develop new features and feedback - but they needed to develop more freely to meet and capture the outside market. Brad talks about the importance of sticking with the vision and focusing on your prospective customers. 1:03:10 Brad has grown the company with triple digit growth the last 3 years in a row - and began paying back the investment. Brad talks about the balancing of growth with profitability - especially in a growth market. 1:06:00 Now in his early fifties, Brad wants this to be his last ‘necessary’ entrepreneurial venture - starting to think more about body, mind and longevity. 1:09:50 What’s Brad's ‘go to advice’ for aspiring entrepreneurs? You’ve got to have passion first and foremost. Second, you must have a compelling value proposition with customer validation. If you don’t have those two things, passion and value, do not proceed. 1:15:30 Allen thanks Brad for being on the podcast - his rise-fall-rise story is cautionary, inspirational, and now available to others to learn from and be inspired. Direct Mail 2.0: https://directmail2.com Plan Your Start: https://www.planyourstart.com

Probably no other startup founder has made the cut at TechCrunch Disrupt, NPR's How I Built This fellowship program, and Babson's WIN Lab. But Lizia Santos is not like any other founder. She built a travel tech startup as a non-tech entrepreneur while simultaneously a mom to three little ones. But she almost lost it all, ran out of money and had to start over. She was ridiculously resilient and came back better and stronger. Now despite the pandemic, her travel platform is growing and expanding internationally. Hear her story, how she did it, what she learned and wants to pass along to aspiring entrepreneurs. SPONSOR: SecureStartup (https://securestartup.com) - Securely and efficiently manage all of the documents between founders and investors.   Opening: Allen & Lizia are on opposite sides of the Florida peninsula. Lizia in Orlando near the Space Coast, Allen in Tampa on the Gulf Coast. 4:05 Lizia gives the origin story of City Catt. She was a journalist with a big idea for better travel. She is from Brazil and travel was always a big part of her life and family growing up. 7:10 One day Lizia and her Dad were discussing their passion for travel. Lizia had her ‘aha moment’ - how can people get access to local information when visiting a location where they don’t know people? 10:40 She did her competitive research and found no websites or apps that did exactly what she was envisioning - there were personal guide solutions but those did not include background checks. This did not feel safe and family friendly. 12:15 Discussion - what’s the first thing you should do when you want to start a software, web, or app company? Lizia describes how she did it wrong by jumping right in to build the product. 14:50 From feedback she would have discovered that her first version could have and should have been much simpler than what she was building. 15:50 Discussion on the non-coder founder dilemma of when and how to work with programmers. 23:40 Allen asks about the dark period when the project was not coming together, cash was running out - how did she cope and pull through. 26:05 Lizia talks about what she had to do personally to survive the difficult time - she brought back her exercise, diet, family, and faith to overcome the stress. 29:30 Lizia is not a proponent of going all-in on your business at the expense of personal health and balance. You need to be equally as intense with your personal life and health as you are with your startup. 30:25 You wouldn’t sprint the first several miles of a marathon - because if you do, you won’t finish the race. 33:50 Allen and Lizia are both TechCrunch Disrupt alum. Amazing experience, amazing connections. 36:10 Growing up in Brazil, Lizia talks about being a pastor’s daughter, a go-getter and a big dreamer. 41:35 Met her husband at a wedding in Boston. Stayed there and started a family until moving to Orlando, her son’s asthma was not good with the cold weather. 48:00 Discussion on how she inadvertently raised seed capital from family. 49:32 While building City Catt, Lizia lost her tech team and ran out of money, and without a working prototype. 52:10 She realized she needed help and mentors. She applied and got accepted to the Babson WIN Lab. There she was challenged to use her resources and creativity. 55:20 WIN Lab taught her to set short-term reachable goals - and believe in herself as a CEO. As a woman and a mom, you are a natural multi-tasker - use this skill in your startup. 1:01:50 The WIN Lab experience woke up the SUPERWOMAN inside of Lizia - felt she could conquer the world. 1:02:20 HOW I BUILT THIS fellowship summit opportunity came up - 16 fellows will be chosen. Lizia believed she could be selected - and then she was. 1:05:47 Met Airbnb co-founder Joe Gebbia at the registration sign in table and had a great one-on-one conversation - fellow travel tech founders! 1:08:30 Lizia and Allen talk about the importance of being bold and taking chances. 1:10:00 Being authentic and honest with your startup’s journey, especially when small and vulnerable, people are drawn in to help you. 1:14:00 Lizia builds her team on skills, personality, and culture fit - not resume. 1:16:00 With the pandemic, Lizia shares how her user's needs have elevated so the level of City Catt service has been elevated also - more trust and transparency. 1:20:25 City Catt also offers a trip planner that works seamlessly with the City Catt full experience - she calls it a ‘Social Trip Planner’. 1:22:30 Lizia says she is now addicted to the startup life - pivoting, improving, and living by the lean startup method. 1:26:45 City Catt is now international - opened by an opportunity with the Olympics in Japan. 1:29:05 SUDDEN INTERRUPTION! A very delicate off-camera negotiation unfolds... 1:30:55 Lizia answers Allen’s final question on how does CityCatt drives traffic and leads? City Catt: https://www.citycatt.com Plan Your Start: https://planyourstart.com

Growing up in a tough neighborhood and making it to college as the first in his family, Rodrick DeBose beat the odds. He received his bachelor's degree and with only $2,600 of debt - but decided he didn't want to work a nine-to-five. He wanted to work for himself and own his own business. So he worked his way up from valet to owning his own parking and shuttle business to now owning rental property and a personal training business and a financial consulting business - helping others stay out of bad debt (use good debt) and start businesses. Hear Rod's story and how he uses Instagram for business ideas and key connections - and how he retired undefeated in his short professional boxing career. SPONSOR: SecureStartup (https://www.securestartup.com) - document management between startup founders and investors. Opening: Rodrick is father of 3 girls. Allen & Rod met years ago. Rod owns several businesses and was a professional boxer for a short time - retired undefeated. 2:20 Discussion on good debt and bad debt. Rodrick talks about the difference and gives examples from his own life of business and asset ownership. He now coaches others. 6:30 Rod talks about the ‘bad debt system’ and helping people stay out of it - easy to get into, very hard to get out. Rod graduated college with only $2,600 in debt. 8:05 Rod talks about the difference between a business with few employees and businesses with many employees - and how he parlayed the profits of his parking and shuttle businesses into launching new businesses. 12:00 Discussion on starting a personal training business, the uncertainty of income and the required dedication. 13:55 Rod talks about growing up in Fort Myers, FL. He didn’t know how rough his neighborhood was until he went back to visit from college. Rod decided he didn’t want to be a statistic. 18:15 His best business role model growing up was his father who owned a small business. 20:12 Rod was the first to go to college in his family, he had to figure out for himself (no one told him or helped him) how to test, apply, and make it. Now he helps others like him figure out the process and not miss the window of opportunity. 21:52 Rod traveled a lot while in college to see the country, didn’t want to regret or have ’could have’s’ or ’should have’s’. Actually came back home for a semester and that was scary because often we don’t go back. He went back. 24:30 Rod graduated with a degree in Criminology from University of South Florida, but knew he wanted to be his own boss, didn’t want to get a job. He already had the entrepreneurial mindset. 28:10 He worked at a valet to help make his life expenses - almost quit the first day! Instead, he grew it and it became his first start up. Allen shares how many entrepreneurial friends he has that started in valet. 30:00 From valet Rod learned to be outgoing and dug deep to find the strength to expand his personality and his customer service disposition. 34:15 Influential people attend the Bucs games and Rod valeted for them. He was invited out to a game by a very successful businessman. 36:00 This person became Rod's friend and mentor. Follow up meetings included building a plan to start his business. He taught Rod how the successful use 'other people’s money’. Rod has used this technique with his recent home renovations and rental property setup. 40:42 He bought into a franchise of Super Shuttle and this was quite successful from a revenue generation perspective - gave him a breakthrough financially. 43:00 He exited this to pursue a business closer to his passion - he became a physical trainer and financial consultant helping others. 45:00 Rod decided to help others with the skills to improve their personal credit. Personal credit and business credit are extremely different and knowing the power behind each can improve your financial situation. 47:30 Most people who know wealth know the separation of personal and business assets and credit, most average people and even those with high salary incomes do not know how this works. Reference to the book Rich Dad, Poor Dad by Robert Kiyosaki. 49:35 Rod gets a lot of business ideas and connections through Instagram - Instagram is powerful, found his number one business mentor there - has found business partners and of course customers on Instagram. 56:00 Allen & Rod wrap up by talking about Rod’s boxing career, the physical, the fun, the technicalities, and the business side of the sweet science. Rodrick DeBose Instagram: @rod_d1fitneess Plan Your Start: https://www.planyourstart.com

What was it like to be on the ground floor of Toms Shoes, part of the early team at Spanx, and then leave to start your own textile technology company while a mom and raising a family? Well, that’s been the adventurous and inspiring life so far of Mary-Cathryn Kolb and in this interview she talks about her journey and the pursuit of big things. She shares advice and learnings from her career and talks about risk-taking and the insatiable, inescapable entrepreneurial mindset.   0:07 Allen and Mary-Cathryn are both from the state of Georgia - Mary-Cathryn from Thomasville, Allen from Savannah. 3:47 She lives in Atlanta now and has pitched and developed key relationships at the annual Venture Atlanta conference - https://ventureatlanta.org. 8:50 How do natural-born entrepreneurs see risk? Mary-Cathryn says “we don’t”. It excites and energizes us. 10:35 If someone had told her how hard it was going to be and all of the things that would go wrong - she wouldn’t have believed and would have kept going. That says it all about the way natural-born entrepreneurs process risk. 12:17 She lost a co-founder and most doubted the company could or should move forward. She never considered stopping. 14:00 Are you wired to be an entrepreneur or can you learn to become one? Mary-Cathryn has always known she was wired to be one. It’s her “north star”. 14:47 There’s a spectrum of entrepreneurship, the moderate risk end and the massive risk end of the spectrum. 16:55 If you go for high risk, high reward, you must be mentally tough and a little lucky. There’s either win or lose on that end of the spectrum, no in-between. 17:45 If you think you can be happy working for others, then by all means do that. There is too much romanticism in entrepreneurship as viewed from the outside. 18:40 If you are wired this way, to be a risk taking entrepreneur, then you probably don’t have a choice but to pursue it. 21:40 She explains how, since she was a little girl, there was never a question that she wanted to do big things and was always enterprising. 22:30 Allen & Mary-Cathryn discuss ‘failure’ and how it’s often celebrated in entrepreneurship but in fact ‘fear of failure’ is a strong motivator and failure should be avoided at nearly all cost. 26:28 Mary-Cathryn talks about growing up with a twin, her college experience at SMU, graduating and going to Los Angeles, then New York to pursue an acting and vocalist career - her childhood dream. 31:34 But it was feast or famine and it’s where she learned about ‘financial runways’ and frugality. She was offered a position with a major designer, so she relocated to New York - her first project was with Beyoncé! 38:35 While in NY her college friend from SMU, Blake Mycoskie, called and asked her to work for Toms Shoes on the ground floor. 40:45 Later, Spanx called, recruited to be one one of the first 30 employees. So she relocated to Atlanta, her husband enrolled at Georgia Tech for his MBA. 42:15 She explains how special the experience and culture was in the early days of Spanx - an amazing sisterhood amongst that early team. 47:10 But with time came new leadership and change. She didn’t feel the changes were best for the team and customers. She felt she had to speak up and take a stand. She knew she’d either be heard or be let go. She was let go. It was her Jerry Maguire moment. 51:20 Discussion on how hard it is for those with intense entrepreneurial mindsets to last very long inside of someone else’s company. And when she took that stand, she had no idea what was on the other side, no backup plan. 55:00 There was an intense emotional hangover after leaving, she needed a break to reboot, but knew immediately that she would start something of her own. 56:50 So brrr was born and with a strong commitment to product, company culture, and shared ownership. 58:50 Working with a polymer scientist and textile engineer, a ‘cool to the touch’ fabric (not just polyester moisture wicking) was developed - patented “Triple Chill Effect”. 1:05:45 She explains brrr is an “ingredient” brand - embedded into fabric of major brands you already know. 1:06:45 Initially designed for women but now brrr is embedded in menswear also. Bed, Bath, & Beyond now carries ‘cooling sheets’ powered by brrr. Her newest project is bringing a much needed cooling effect to children’s car seats! 1:10:00 What advice for someone creating in the clothing or garment space? Mary-Cathryn says make the business as lean as possible and go big on social media! 1:14:00 Take the risk of entrepreneurship if it’s for you but know that it’s lonely, will take twice as much money and time that you imagine - so get a support system. 1:15:30 This is a personal journey, she has three young daughters and wants them to see up-close what a successful woman entrepreneur and working mom looks like and that family and career can coexist if that’s what you want.   brrr: https://brrr.com Plan Your Start: https://planyourstart.com

Art Fyvolent gave it his everything in trying to work for others. He had a very successful early ad agency career but he knew he was meant for more and meant to work for himself. He finally broke away to start his own agency, sold it years later, then took a year off to recharge and reset his life. He came back and became an idea machine and 'multipreneur'. Now Art has Squirrel Ventures which is a collection of all his startups at various stages of growth and development. At this stage of his entrepreneurial life, Art gets to engage in multiple ventures at once while also championing society-improving projects that ultimately put a 'ripple in the universe' and leave a legacy of helping others.   0:30 Art starts by saying he identifies with Allen’s new book “Quit to Start” because he has been all 3 types of entrepreneur - Type A, Type B, and Type C. And a good laugh at how Allen and Art are wearing the same shirt for this interview. 2:10 Art is a 'Multipreneur.' - many different startups at various stages. He created Squirrel Ventures to hold everything - and sometimes just domain hoarding. 3:40 Is Multipreneurship a gift or a curse? Art enjoys switching brains from one thing to another. He likes to build up a team, hand it off, which frees him up to pursue other ventures. SPONSOR - SecureStartup (https://www.securestartup.com) - managing all of the important documents between founder and investor. 7:30 Art was an early adopter of Internet marketing. He built a successful agency, building online presence for some of the biggest brands in the U.S. 9:30 Starting out you need to focus on one thing. Later, with experience and connections, you can do more. 11:05 Discussion on two lanes of motivation for entrepreneurship - be your own boss or create something big. Art adds a third that can come later, helping others. 12:15 Art’s great-grandfather was a street entrepreneur selling fruits and vegetables. His grandfather came out of law school and directly started his own practice. His father went out on his own also. So Art feels that it's in his DNA, it’s what he's supposed to do. 14:30 Allen asks if while Art was working for others, did he feel something was off and that he should be working for himself - Art emphatically says yes. Even in college, he started his own side marketing company. 16:00 Art took his shot working for an ad agency in Atlanta, was doing quite well but realized he couldn't climb the ladder all the way to NYC - so he moved back to Florida and went to work for an agency in Tampa Bay, took business classes by night at USF. 19:14 Art then moved up to a bigger firm in the area - but he had an 'independent streak' and one day talked back to the boss and got fired. He went to work for a competitor for several years. But he just couldn't take it anymore. 20:00 He went home one day to his pregnant wife (and their home in mid-renovation) and said that he had quit his job and was starting his own company. Allen shares his first epic quit which was similar - he and wife had just moved into their first starter home and had a brand new baby. 22:40 Art's first client stiffed him for $6K. That was grocery money, baby money, everything money. He got help from a supplier to cover this. 24:00 Discussion on the generosity from people during the early stages of business. Clients, suppliers, and partners will recognize your drive and will want to help you. 25:55 Art landed one of the largest accounts in Tampa Bay while working out of his home, they took a chance on him. That put his small business on the map and gave other large companies the confidence to sign with him. He went on to grow and sell the business years later - and then took a year off. 29:20 Founders need time to detox and re-energize after selling their business. Art came back with a different mindset. 35:40 Fun discussion on domain hoarding - at one point Art owned 1,600 domains. It's one of the best ways to capture a business idea. 38:40 Art has several active ventures such as iGrew - security-first parent portal to capture and safely share your child's life; Smiling Dog CBD for Pets; Redneck Jobs for blue collar jobs; and more. 43:50 You can’t pursue multiple ventures without an income base - a few of Art's ventures are generating the income he needs to do this. 46:00 Art stresses that entrepreneurship for him has never been about the money. 48:50 He likes to put a 'ripple in the universe' and contributing to society. Art discusses his passion for pit bull rescue and a local refuge facility for large dogs. 55:10 Being a successful entrepreneur allows you to one day work on issues important to you. Art wants to leave a legacy of helping others - including animals. 57:00 Entrepreneurship is maybe the only path to create the significant time, money, and resources needed to make a really big difference in the world - put a ripple in the universe!   Squirrel Ventures: https://squirrelventures.com Plan Your Start: https://www.planyourstart.com

Winning $100k investment from Steve Case and being named one of "100 Powerful Women" by Entrepreneur Magazine didn’t come easy for Ashlee Ammons. She left her great job and income to be an entrepreneur, fought self-doubt, rejection, and the challenges of not looking like a typical tech founder when pitching and meeting with investors. In this interview she talks about all of that and how she and her mother and co-founder raised their first $1M with smarts and determination. 1:00 Ashlee & her tech startup Mixtroz are in Birmingham, AL - discussion about the special tech & investor ecosystem there. 2:40 Nashville was great but the opportunity in Birmingham was greater for what they needed to accomplish as a company. 3:40 In 2017, Ashlee and her co-founder (her mother, Kerry Schrader) went to Collision Conference in New Orleans. They wore matching t-shirts, "Black Female Founder, Fund Me - Got Seed?". 4:40 The t-shirts caused a stir, but the event yielded three big connections - an article in Forbes, an invite to Creative Startups pitch competition in New Mexico (which they won), then to Copenhagen (won there also), and most importantly, met the future executive director of Velocity Accelerator in Birmingham. 7:20 In 2018, won Steve Case’s Rise of the Rest $100,000 competition in 2018. Went on to raise more than $1M but it was hard. Fundraising is brutal, it takes invaluable time and energy away from your startup. It can also be soul crushing, similar to the superficialness of a beauty contest. 8:50 White males seem to raise six figures in about 3 months on average. White women maybe 4-5 months, women founders of color, at least 6 months. 9:30 Ashlee talks about how her and her mom had to be mindful of their appearance when they were raising money. Ashlee talks about how she keeps her hair in braids-dreads because (a) it’s ridiculously hot in the south, (b) it’s low cost and (c) it’s low maintenance - smart for a bootstrapped entrepreneur. 10:50 Allen asks Ashlee her secret to public speaking on big stages. She says it’s preparation, memorization, and practice, practice, practice. 14:00 What if you don’t look like a typical tech founder? Ashlee and her mother are non-technical black women founders building a tech product startup - none of that is typical. 17:50 Ashlee suggests founders find a partner over the age of 40, especially a woman - especially one like her mom that had a successful executive business career. 19:40 Women over 40 are often highly energized, motivated, and an invaluable source of experience and determination. 22:00 Ashlee and her Mom took personality assessment tests that identified their strengths and weaknesses, helped them with roles and responsibilities. 23:20 SPONSOR: SecureStartup (https://www.securestartup.com) - Secure and easy way for startups to share documents with investors. 26:20 Ashlee was determined to be successful since a child. Her parents worked hard to set her up with opportunity. Her grandparents did the same for her mom. 30:00 Through a connection, Ashlee became LeBron Jame’s first intern. This demonstrates the power of relationships and networking. 33:20 Then with the help of LeBron’s connections, she became an event planner in New York. She went there to do all the grunt work she could get, to learn and build relationships. 38:10 Then one day she had a lackluster experience at a conference - networking disaster. She called her Mom that night and funny enough, her mom had just had a similar experience. What could solve this problem? Mixtroz! 42:40 So she made the leap, moved to Nashville, moved-in with her mom, loss of independence and income. 45:00 Ashley says that “comparison is the thief of joy.” Startup depression is real - self-doubt, isolation, and professional loneliness. 47:00 Friends and family don’t always understand, can be non-supportive (you’re going to fail) and some envious (you’re going to succeed). Ashlee says the anxiety is real and feels like a rollercoaster. 49:00 Ashlee and her Mom bootstrapped - put in their own money, then small investments from friends and family - another advantage of having an over-40 partner, her mom’s connections had more investable capital. Mom would not allow large investments from friends and family. 55:10 Is entrepreneurship a 'sport for the elite'? Access to capital, connections, and generational wealth is a big hidden success factor. 59:00 Ashlee and her Mom have had to fight to get their place at the table - even when they had to pull up their own chair. 1:03:00 Are women founders (and founders of color generally) over-mentored and under-funded? Yes. And Ashlee explains that women founders and male founders of color, it feels like they'll only get one shot. 1:07:00 Ashlee closes by talking about the opportunities and adjustments during COVID-19, their current growth capital raise, and the exciting road ahead for Mixtroz. Mixtroz: https://www.mixtroz.com Plan Your Start: https://www.planyourstart.com

This week's guest is Steve MacDonald. He started without money or connections but found a way to build a startup to over $100M in revenue and a 9 figure exit. Now he's an investor himself having personally invested in over 120 companies and counting. In this interview we talk about what it takes to be a successful company builder and then a successful angel investor. Steve breaks down how founders should approach capital raising and he describes what he will be looking for with his new investment firm, MacDonald Ventures.   0:05 Allen finds Steve in Aspen, CO getting a break from the Florida heat and humidity.  2:30 As an entrepreneur, better a maverick or maven? Steve says knowledge (maven) is power, but not without action. Steve will take a maverick over a mavin every time. 4:00 To be a successful entrepreneur, you have to be great at a lot of little things, not just a specialist at one thing.  5:40 How does an entrepreneur balance being an independent-thinking maverick with also being a team-player? 7:00 Steve says a founder building a team or raising capital must be flexible and open-minded. 11:15 - SPONSOR: SecureStartup (https://www.securestartup.com) - Secure and easy way for startups to share documents with investors. 12:40 - Steve sold his company in 2017 with a 44x return on investment to his investors. He's had several other startups with successful exits prior and along the way. Prior, he worked for a Fortune 500 company at which he rose the ranks. 15:00 Steve has personally invested in over 120 early stage companies. Steve discusses the importance of 'diversified portfolio' approach to early stage angel investing.  18:30 Steve talks about what a 'syndicate lead' investor - and strongly recommends that approach to new investors. 20:30 New investors typically do not have exposure to enough opportunities (deals) to make a truly informed investment decision. Plugging into an existing funnel and co-investing alongside syndicate leads is the best strategy 23:05 Steve says that it typically takes 7-10 years before an early stage investor receives a return - and it's typically not until year 7 that a company hits the acceleration phase. 24:28 And when a company starts to accelerate, the founders are tempted to cash out. But if they stick with it, the win to both them and their investors can be much larger. 26:55 Investors that understand and accept the long game are more relaxed, which is good for their co-investors and the entrepreneur. 27:40 Years 3-4 are often gut-check years, for the founders and for the investors - can we be patient and get to the acceleration phase? 29:20 Why tolerate the long game as an investor - because of the big home runs that can happen. But you need a portfolio, you don't know which one(s) will breakout and which ones will fail. 31:00 MacDonald Ventures: Steve discusses his new investment company and mission to find the world's next phenomenal tech companies. The 5 attributes looking for in a founder: Realistic, Humility, Traction, Preparation, and Commitment. 33:00 Realistic - when a founder is unrealistic (on many things including valuation), it hurts their opportunity within the investment community - because investors talk.  37:55 First-time founders don't always know how to 'set themselves up for success'. 38:50 Why is humility important in a founder and how does it manifest? 40:40 What should founders think when they are being passed on for funding? 46:25 How much traction is needed to attract a professional investor? 50:33 Steve talks about how CEOs need to be focused on asking the right questions and setting the right metrics. 52:20 No matter how great the product, business, or team - you cannot be unprepared for an investor meeting. 56:05 Steve talks about the importance of commitment and perseverance - this is probably number one of all attributes. 56:18 Steve says being an entrepreneur is like "getting in the ring with Mike Tyson every day for 10 years." 59:05 Steve talks about how he was not raised in wealth, just the opposite, and had no investor connections when he started. He describes how he did it - and it wasn't asking people for money, and he was able to raise $5 million dollars. 1:03:26 Courting investors is a relationship building process and you shouldn't behave as though you expect a check in the first meeting. 1:04:45 How to use the cascading 'herd mentality' approach to raising money. 1:10:10 The kind of businesses that MacDonald Ventures will typically be interested - business process automation will always be high on the list. 1:12:35 Steve explains why consumer product companies find it so hard to gain investment - and the Twitter origin story that few know. 1:16:26 Parting message from Steve - we are in difficult economic times right now but this is when great companies and great entrepreneurs shine through with perseverance and creativity.   Plan Your Start: https://www.planyourstart.com Another interview w/ Steve: https://bit.ly/3jgu5Jn

Christy Brown, a three-time exited founder and now investor, mentor, and advisor to early stage companies, especially women and minority entrepreneurs. Hear about how Christy learned business acumen from her entrepreneur grandmother and tenacity from her mother, raising her and her sister solo while working. She goes on to excel at male-majority Georgia Tech and then a skillful run of working for big corporate, to startup founder, to acquisition, back to corporate, then back to startup founder - rinse and repeat 3 times. Now she is an investor, volunteers for the causes she cares about, and helps women and underserved founders navigate the waters of early stage business and capital-raising. 1:50 Discussion on how first-time founders don’t always understand the long game needed to raise capital, months or years of relationship building before a check is written. 2:30 Staying in touch with potential investors is critical. Christy says getting monthly updates from companies is what she values the most. 4:00 Discussion on what it says about a founder that takes the time to send out monthly updates to current and potential investors. 5:30 If a potential investor has a great feeling about you and what you’re doing, they are likely to introduce you to someone (else) that could invest. The founders that know how to communicate effectively are the ones that win. 7:00 How many mentors does an entrepreneur need? If you are growing as a company, it would be normal that you outgrow your mentors along the way and need new mentors as you grow. 11:50 SPONSOR: Executive Launch (https://www.execlaunch.com) – from corporate executive to startup founder. 13:00 Christy’s bio: President Launchpad2x, advisor to Tone Networks, venture partner w/ Republic crowdfunding, mentor with TechStars, board member with Venture Atlanta Conference, Board Ambassador with American Cancer Society, former chairperson of C5 Georgia for teens, and advisor to several other non-profit and social cause organizations. 14:05 Christy is in the 3X club having built and sold 3 companies a.k.a ‘exits’ that provided her financial gains that each time enabled her to recharge for another run. 15:00 She lived a playbook of going from corporate to startup, back to corporate, then startup again. This is a winning strategy for exits and acquisition. 18:05 Allen & Christy talk about how they both struggle to watch Shark Tank the TV show 22:10 Christy talks about the influence of her grandmother and mother. Her grandmother was one of the first women entrepreneurs in the Atlanta area. Working mother of 4, amazing storyteller, stood in the boardroom with men, didn’t take no for an answer. 25:35 Christy talks about the influence of her mother. She demonstrated work ethic, tenacity, and competitiveness. 27:40 At 7 years old, Christy got her first computer, a Commodore 64 and started programming. 29:35 She didn’t realize she was unique as a young girl that liked science, complicated math, and computers. 31:40 Christy wanted to be a fashion designer, wanted to study textile/fiber engineering at Georgia Tech. An internship with telecom giant WorldCom steered her to electrical & computer engineering. 34:20 Christy talks about often being one of the few girls in class at Georgia Tech and the challenges. 37:10 Her first job after graduation at WorldCom, what she learned from their massive bankruptcy. 39:10 Then her first startup, a web development and e-commerce company. Just one starting client and no money. Later cashed out to her partner and took a year off, competed in several triathlons around the world, contemplated what to do next. 45:30 Recruited to open an Atlanta office for a large staffing/recruiting company. Financially exited later to open her own firm – which was then acquired a few years later by a large company. 50:00 Able to financially exit again and recruited to be a senior executive with ADP. After four plus years, left to start investing and create another startup. 54:40 Began dedicating more time to helping women entrepreneurs and executives – the ‘broken rung’ problem. 57:00 Christy describes the challenges for female founders and founders of color. 1:04:20 Discussion on the unique psychological challenges of women and minority founders – and the dramatically disproportionate lack of investment. 1:06:50 Studies show that women founders outperform male founders in investor ROI. So why are women severely under-represented on both sides of the table? 1:09:50 Founder confidence isn’t the only issue, it’s often allowing for the founder’s ‘authentic self’ to shine through. 1:13:10 Final thoughts from Christy on how anyone can be an entrepreneur if they set their mind to it. It’s similar to endurance running and triathlons. Not everyone can be a competitive sprinter, but nearly everyone can be a competitive endurance runner or triathlete if they commit. Christy's LinkedIn Page: https://bit.ly/3egZ4RX Allen's Website: https://www.planyourstart.com