the idea: to become the brand manager for a nfl super star and extend his brand and vision beyond the field.

the gems: kelvin took a chance on me – a person that never worked with a professional athlete in this capacity.

the lemon: i didn’t take the time to truly understand his core values and how those values aligned to off-field business ventures.

the result: kelvin terminated my services and i lost my opportunity to work with him and his other team mates.

lesson learned: you must dig deep with your clients to truly understand how their personal values cascade into how they run their business/brand. also, if you’re new to a segment of business and someone gives you a chance – get smart, hire a mentor and pay close attention.

the idea: ion360, my IT firm to provide it services to kipp indianapolis.

the gems: i was awarded a maintenance contract with the school and serviced the school for one year.

the lemon: kipp did not renew its contract with ion360 based on cited budget constraints. kipp indianapolis decided to invoke a law suit against almost 18 months after we concluded our relationship. the filing claims ion360 promised “responsive service and rapid resolution” to technology issues and problems, along with 24/7 support, but did not deliver. yes, they decided i didn’t deliver 24/7 support, almost 18 months after services amicably concluded…

the result: the lawsuit was withdrawn. myself or ion360 were not found guilty of any allegations expressed in the lawsuit.

lesson learned: you must have tightly constructed contracts and always document everything! invoke terms and time limits on post termination clauses.

the idea: create a k-8 charter school to provide indigent students access to robots, wind turbines, apple technology and a thematic curriculum

the gem: the school was launched with everything i built it for!

the lemon: someone i entrusted expressed to the board that i defrauded the school out of funds. the allegation came about whilst i was conveniently out of the country for almost 2 weeks. when i arrived back in the u.s., i was on the news, and was told never to step foot back on school property. i never had the opportunity to defend myself nor was an objective investigation rendered.

the result: of course, it was established (via arbitration) that no such “fraud” occurred and i further left the proceedings net positive. even though proof was evident, i was removed from management of the school and essentially “erased” as co-founder.

lesson learned: invest in a legal team that will establish a corporate structure to protect founding interests, deeply research the team you build with and create a solid culture. be clear on revenue allocations, capital expenditures and always use the best fiduciary management practices.

the idea: to create the first web based, cloud hosted, subscription based sis (student information system) that aggregated student data, educator data and operational data

the gem: i got an investor!

the lemon: i contracted with my long time “friend” to write the software. he never wrote the software and he netted approximately $40k of my investment funds.

the result: i had to pay back the investor to avoid being sued. the software never launched and my “friend” relocated to costa rica at the time. i was also accused of orchestration the bad investment even though i was left high and dry.

lesson learned: even when working with friends, you still need contracts! establish payment and project milestones as well as build in contingency and exit strategies. use weighted charges back and incentive clauses for missed/completed deadlines by vendors.

the idea: to offer politicians interactive kiosk platforms that could be distributed at campaign sites to collect constituent data, input and donations.

the gem: i was able to build a prototype

the lemon: my idea was not 100% developed nor did i have any political relationships to leverage.

the result: never launched.

lesson learned: take your time and plan! research, plan, research and plan more! establish relationships within your target market.

the idea: to open a retail shipping store that offered design services.

the gem: i was able to successfully open two of these stores.

the lemon: i was self-funded (no investors) and i didn’t entertain a full fiscal cycle on the first store before i opened the second.

the result: i ran out of money and closed them both.

lesson learned: build detailed financial models with contingency and exit strategies. slow your damn roll!

the idea: to place advertising-based programming on monitors within indianapolis city buses.

the gems: i got a placement contract with indygo and had agreements with clearchannel. i designed the prototype and afforded to fit two gm hybrid buses.

the lemon: i was arrogant with my approach and thought my idea was the most brilliant idea ever however, it was deemed “stupid” by vc’s in 2004. never got funded.

the result: never made it out of prototype, testing phase.

lesson learned: you have to build a team! you cannot do everything yourself. secure financing/investments before engaging the business strategy. you cannot run a business on hope and a wish or arrogance!