Start Ugly (with Chris Krimitsos)

What It Covers

Chris Krimitsos, creator of Podfest conference and documentary The Messengers, explains his Start Ugly philosophy for launching business ideas without waiting for perfection, plus discussion of 529 college savings plans and Merrill Lynch pausing advisor trainee hiring.

Key Questions Answered

• •Start Ugly Philosophy: Launch projects immediately without perfection by focusing on why over how. Krimitsos started his documentary seven days before announcing it at Podfest 2016, proving passion overrides technical concerns. Set check-in dates to assess whether to continue, pivot to hobby status, or quit without shame.
• •529 College Savings Strategy: Save approximately $100 monthly per year of college per child starting at birth to fund public university costs. For four years of coverage, invest $400 monthly from birth. Turn investments conservative when child enters high school freshman year to protect accumulated funds from market volatility.
• •Finding the Right Feedback: Distinguish constructive criticism from negativity by evaluating the source's relationship and track record. Accept brutal honesty from people who love and support you, like literary editors who improve work. Ignore feedback from perpetually dissatisfied people who criticize everything without offering solutions or alternatives.
• •Pension Planning Caution: Never rely solely on employer pensions for retirement despite union contracts or company promises. Companies eliminate pensions violently during worst times. Build independent retirement savings through 401k and brokerage accounts, treating any pension received as bonus income enabling early retirement or additional security.
• •Diversification Across Accounts: Holding identical ETFs or mutual funds across 401k, Roth IRA, and brokerage accounts poses no problem. Avoid individual stock concentration like Microsoft or Apple across multiple accounts. Maintain four to five positions spanning large companies, small companies, international stocks, and real estate for adequate diversification.