Stealing from companions is not treated as a crime or hostile action, so Ian isn't really convinced to join for free, give him the money and steal it right back if needed.
The XP reward is the same, regardless of the method chosen.
This is not given as a quest by anyone, but it is something that can be done for additional experience and a new companion.
With an Intelligence of 1, Ian cannot be recruited easily. A minimum Intelligence of 2 (maximum 4) will require the use of Mentats.
Destroy the Mutant leader ·Destroy the source of the Mutants ·Find the Water Chip
Side quests
Become an initiate ·Bust the Skulz gang ·Calm rebel faction ·Convince the Elders to send help ·Destroy the Super Mutants at the Watershed ·Disarm Traps for the Facility ·Dispose of Jain ·Dispose of merchant ·Find the missing caravans ·Find the Water Thief ·Fix the broken T-51b power armor ·Fix the hydroponic farms in Adytum ·Fix the Necropolis water pump ·Free Ghoul prisoner ·Get Gizmo's confession ·Guard the caravans ·Help Irwin ·Join the Khans ·Kill Killian ·Kill Neal ·Rescue Initiate from the Hub ·Rescue Tandi from the Raiders ·Rescue Sinthia ·Save Trish ·Solve Scrapheap's gang problem ·Steal Neal's Urn ·Steal necklace from the Merchants ·Stop the Radscorpions ·Stop Gizmo ·Turn on power for the Glow
Unmarked quests
Blackmail Iguana Bob ·Clean out the Loan Shark ·Cure Jarvis of Radscorpion Poison ·Exterminate the deathclaws ·Free Adytum from the Regulators ·Free the Slaves ·Get weapons for the Blades ·Help Saul ·Improve Shady Sands' Agriculture ·Kill Razor ·Make Poison Antidote ·Obtain more equipment ·Recruit Ian ·Recruit Katja ·Recruit Tycho ·Research important information ·Save Killian's life ·Scout the northern wastes ·Solve Phil's Canine Conundrum ·Take down Decker ·Talk to Katrina ·Unlock the Armory
Cut content side quests
Become a Blade ·Deliver Locket for Romero ·Deliver package from the Gun Runners ·Find Children spy in the Followers ·Rescue Jason Zimmerman ·Stop the Gangs from attacking Adytum ·To Catch a Wisp ·The Search for the Glow ·The Trade Line ·The Wood Cutter's Wife
Rescue Tandi from the Raiders ·Stop the Radscorpions ·Cure Jarvis of Radscorpion Poison ·Improve Shady Sands' Agriculture ·Make Poison Antidote ·Recruit Ian ·Talk to Katrina